[[quoteright:350:[[Film/BackToTheFuturePartII https://static.tvtropes.org/pmwiki/pub/images/bttf_besties.png]]]]
[[caption-width-right:350:Marty and Doc, friends for all time.]]
%%
->'''Silvia Mora:''' The old men are sad characters.\\
'''Mabel Mora:''' I guess. Sort of. They're also the first friends I've had in a really long time.
-->--''Series/OnlyMurdersInTheBuilding''

Two people are good friends. Only, one of them is about twice, three times, -- or even four or more times -- the other person's age! Considering their differences in life experiences and worldviews, how do they relate? What could they possibly have in common? Assuming this is actually a platonic friendship and not [[WifeHusbandry something far more sinister]], or for that matter an overtly stated mentoring situation, intergenerational friendships can be pretty weird. As the RealLife section indicates, while not everyone finds older or younger people completely unapproachable, there's still frequently a gap there.

This can take the form of a young adult from one generation befriending someone old enough to be their parent or even grandparent, such as in the comedy ''Film/FindingForrester''. It can take the form of an adult befriending a misguided or vulnerable youth, as in the French film ''Film/TheProfessional''. Sometimes, the two happen to have more in common than they think, such as having surprisingly similar life experiences. Sometimes the younger generation is more mature, or the older generation is less mature; the latter especially helps writers to dodge away from worrying questions being asked about sexual attraction.

As for how they become friends, it could well be contrived circumstances that bring them together, or a shared life experience. Sometimes it's a teacher trying to help a troubled teen, leading to them becoming close friends. Either way, the situation that leads to their friendship would often be something out of the ordinary, since in real life, people of two widely different age groups generally do not reach out to each other.

Sadly, though, if it's an adult and a child who are friends, in modern stories, [[MistakenForPedophile expect someone to misinterpret it as being sexual]], [[PaedoHunt and violence to possibly result]]. Sometimes the younger one will have an innocent PrecociousCrush on the older one.

This trope does not generally apply if it's a [[ParentalSubstitute parent-child relation]] between the two.

A subtrope of OddFriendship.

Contrast AgeGapRomance and MayDecemberRomance, in which there is a generation gap between romantic partners, and IntergenerationalRivalry, in which there is a generation gap between rivals. Although neither trope is mutually exclusive and can sometimes overlap.

SisterTrope to MayflyDecemberFriendship, which involves friendship between beings of vastly different lifespans.
----
!!Examples:
[[foldercontrol]]

[[folder:Anime & Manga]]
* ''Anime/DotHackSign'': Bear (middle-aged writer) and Mimiru (high school student). Gamers from different generations playing a virtual reality [=MMORPG=]. "You know, when I was your age, we actually had to use graph paper to map out the mazes in games." "You ''are'' old."
* ''Manga/AfterTheRain2014'': Kondo, a 45-year-old divorcee, insists that he sees his relationship with the much younger Akira (a 17-year-old highschool student) as a non-romantic friendship. She isn't thrilled about the "non-romantic" part.
* ''Anime/ArabianNightsAdventuresOfSinbad'': Sinbad and his two friends Ali Baba and Aladdin all greatly differ in age, with Sinbad being a child, Ali Baba being somewhere in his twenties, and Aladdin being an old man of undetermined age.
* ''Manga/BlackButler'':
** Vincent Phantomhive (late 20´s?) with Undertaker ([[ReallySevenHundredYearsOld at least a century]]) and Baron Kelvin (in his 50´s).
** Ciel (13) has a VillainousFriendship with Sebastian (a demon). Also he´s at least in good terms with the aforementioned Undertaker [[spoiler:until the Campania Arc]] and Lau (early 30's).
** Agni (an adult) with his master Soma (late teens) and tries to be a friend with [[ReallySevenHundredYearsOld Sebastian]]
* ''Manga/{{Bleach}}'':
** Nel, who is a child, and Ichigo, a teenager. Then, we find out that [[spoiler:Nel is in fact the former Tres Espada and much older than Ichigo.]]
** Captain Hitsugaya is the Shinigami equivalent of a TeenGenius and looks like a 15-year-old. Captain Ukitake is at least a 30-something-year-old [[ReallySevenHundredYearsOld in looks.]] Ukitake wants to strike one of these with Hitsugaya. HilarityEnsues.
* ''Manga/BLMetamorphosis'' is about an unlikely friendship between 17-year-old Urara Sayama and 75-year-old widow Yuki Ichinoi; when Ichinoi picks up a volume of [[YaoiGenre BL manga]] out of curiosity and finds she enjoys it, she goes back to the bookstore to get more, and forms a friendship with longtime YaoiFangirl Urara from there.
* ''Manga/CaptainTsubasa'':
** Roberto (late 20's/early 30's) and Tsubasa (12 at the start of the series).
** Also Hyuga (12-13 at the start) and Kouzou Kira (mid to late 30's).
* ''Manga/CardcaptorSakura'': Sakura (10) and Kaho Mizuki (20s). All of [[spoiler:Eriol]]'s friendships might count as well, taking ReallySevenHundredYearsOld into account.
* ''Manga/CaseClosed'':
** The title character (a 16 year old in a 7 years old body) with a lot of characters: all the police officers, several FBI members (mostly Akai and Jodie), the detective children, Dr Agasa... In universe, several characters think he has this kind of relationship with Heiji Hattori (who is really of his same age).
** The 16th film, ''Anime/DetectiveConanFilm16TheEleventhStriker'' has Kazumasa Nakaoka (24) and Tomofumi Motoura (about 10-11 years old), who was an aspiring soccer player. [[spoiler:It doesn't end well.]]
** In the anime, Heiji himself has one with the 30-something restaurant owner Heishirou Bizen. [[spoiler:Sadly, [[SacrificialLamb Bizen is stabbed to death]] in the seventh NonSerialMovie.]]
%% ** Tooru Amuro (Rei Furuya) with 'Hell Angel' Elena Miyano.
* ''Manga/{{Claudine}}'': The psychiatrist is at least middle-aged when he meets the ten-year-old Claude. Despite the large age gap, they both share a lasting friendship. The psychiatrist explicitly refers to Claude as a good friend in the ending narration.
* ''Manga/DrStone'': Senku and Chrome (mid-teens) and Kaseki (60s), thanks to their mutual love of science and crafting. They get a rather sweet FriendshipMoment in Chapter 57, where Kaseki laments that he never had friends growing up; Chrome says that they're his friends, and rejects the age difference by saying "What does that have to do with anything?", which brings Kaseki to tears.
* ''Anime/DragonBallZ'': Gohan and Krillin, particularly in the Namek saga, where they spend a lot of time working together trying to think their way around the much more powerful villains. The weird thing is that Krillin isn't much taller than the ''six-year-old'' Gohan.
* ''Literature/{{Durarara}}'': Shizuo Heiwajima (24) tends to develop friendships with people that are out of his age range, such as Simon (late 40s to mid 50s), Akane (10), the [[spoiler:Orihara]] twins Mairu and Kururi (15), and Celty ([[ReallySevenHundredYearsOld 200+]]).
* ''Manga/Eyeshield21'': Sakuraba (a high school student) and Torakichi (a grade schooler) who is Sakuraba's biggest fan and one of Sakuraba's main motivators for improving himself.
* ''Manga/FruitsBasket'':
** [[TheStoic Hatori]] and [[{{Keet}} Momiji]]. They seemed to bond after Momiji was forced to leave his parents as a child (when Hatori was 20), and they remain close at least until the beginning of the series. Hatori probably took it upon himself to be a ParentalSubstitute, but oddly enough, Momiji still sees him as a friend, not a father figure. They turn out to have [[StoicWoobie quite a bit in common]].
** Also, Tohru (16) with Shigure, Ayame (same age as Hatori) and Ritsu (a college student).
** Tohru's mother with Arisa Uotani, Tohru's friend.
* ''Manga/FullmetalAlchemist'':
** Cute, PluckyGirl Xingese princess May becomes good friends with the HeroKiller, Ishvalan ex-priest Scar, who is on a RoaringRampageOfRevenge. It helps that May is a HorribleJudgeOfCharacter.
** Roy Mustang, age 29, mentored by and (at least to appearances) pretty good friends with General Grumman, who is old enough to be his grandfather. (Which is definite, since he [[WordOfGod is]] the grandfather of Mustang's [[VictoriousChildhoodFriend close friend]] Hawkeye.)
* ''Literature/FullMetalPanic'': Sousuke (16) and Kalinin (40-50+ ?). Kalinin doesn't quite make it as Sousuke's father figure (Majid took that role), and is more of a intergenerational [[HeterosexualLifePartners Heterosexual Life Partner]] (though this is most notably during their backstory where they spent more time together - Kalinin shows up a lot less in the present time of the series, though he technically ''is'' Sousuke's legal guardian).
* ''Manga/FushigiYuugiByakkoIbun'': the 20-something Nirusha and the 10-years-old Reipin, with the first helping out the latter to find her inner strength in exchange for her being kind to him [[BecauseYouWereniceToMe when nobody else would]].
* ''Anime/FutureGPXCyberFormula'': 14-year-old Hayato Kazami making friends with several of these; with Bleed Kaga (19), Naoki Shinjyo (17), Knight Shoemach (21), Jackie Gudelhian (20), Franz Heinel (21), Edelhi Bootsvorz (22) and on his team, with Tetsuichiro Kurumada (47) and Shinsuke Maki (19).
* ''Anime/GaoGaiGar'': Mamoru Amani (9) and Gai Shishioh (20).
* In ''Literature/{{GATE}}'' [[ReasonableAuthorityFigure Tarou Kanou]] was an up-and rising government bureaucrat in his mid-thirties, and Itami Youji was a [[HarmfulToMinors troubled junior high kid]]. Both of them met on a street corner when Tarou saw that Itami was reading a Manga and got them into a discussion about their shared love for Manga. Now Itami is [[CrouchingMoronHiddenBadass an illustrious and distinguished First Lieutenant]] in the JSDF, while Tarou Kanou is Japan's Defense Minister who is gunning for the Prime Minister seat, but twenty years since they first met; they are still fast friends.
* ''Manga/{{Gintama}}'':
** The Yorozuya trio. There's Kagura (14) and Shinpachi (16) with their boss/comrade/friend/sorta-like-big brother Gintoki, who's [[ShrugOfGod somewhere in his 20s]]. Kagura even sleeps in Gintoki's closet.
** Also Okita (18) and his beloved captain Kondo (30ish). Hijikata falls somewhere in-between.
* ''Manga/GugureKokkurisan'': Kokkuri is probably a lot older than the 25 years he'd like to claim. Kohina is an elementary student. Nevertheless, even though Kokkuri's acting as a parental substitute, they still consider each other friends.
* ''Franchise/{{Gundam}}''
** ''Anime/MobileSuitGundamSEED'':
*** Mu La Flaga (late twenties/early thirties) and Kira Yamato (16). Later, we get Andrew Waldfeld (late thirties/early forties) and Kira.
*** Also Murrue Ramius (late twenties) and both Kira and his friends (15-16). By the end Natarle (same age bracket as Murrue and Mu) strikes one with [[spoiler:Fllay]] (15) when she [[spoiler:becomes her BridgeBunny after her CharacterDevelopment]].
** ''Anime/MobileSuitGundamWing'': Heero Yuy (14-15) and [[spoiler:the little girl (no older than 8) and her dog]]. [[spoiler:It doesn't end well. Holy crap, it doesn't.]]
* ''Webcomic/HetaliaAxisPowers'':
** Iceland (ageless nation with the looks of a 17-year-old) and Turkey (also ageless nation, looks like in his mid-to-late 30's). More exactly, the ''Manga/HetaliaBloodbath2010''.
** Also France (ageless nation who looks like in his late 20's) andf 19-year-old American tourist Lisa, [[spoiler: the reincarnation of another 19-year-old girl he was friends with... Joan of Arc.]]
** Rome (''dead'' ageless nation with the looks of a man in his 40's) attempts to strike one with his grandson's best friend/boyfriend, Germany (another nation who looks like a 19-20 year old [[spoiler: but ''may'' be "older" than that]]). HilarityEnsues.
* ''Manga/HikaruNoGo'': Hikaru Shindou who is around 12 years old at the beginning of the story, and Fujiwara Sai, who is a couple hundreds years old ghost.
* ''Manga/HisAndHerCircumstances'': Maho Izawa (mid-teens) and Yuusuke Takeshi's (late 20's) relationship starts off as this when she was lecturing her friends, and he notices her leg was bleeding, and he claims he saw see a vision of a lovely schoolgirl holding flowers. [[spoiler:This later becomes a MayDecemberRomance when they started to fall in love and get married at the end of the manga.]]
* ''Manga/HunterXHunter'':
** Isaac Netero, who is at least 110 years old or older, is shown to be friends with many people who are much younger than him. The Juuni-shin/Zodiacs, the Shingen-ryu Kenpo martial artists (including Wing and Biscuit), Morel, Knov, and many other Hunters are mostly adults of various ages. Even old characters like Linne and especially Zeno are not nearly as old as Netero (Netero was already an old man when Linne and Zzigg were young adults and Zeno is 67.)
** The Phantom Brigade have a VillainousFriendship going on and the member vary in different ages. They even welcome Kalluto (10) and have accepted him as their friend...sort-of.
* ''Manga/IAmAHero'': Hideo and Hiromi, [[spoiler:at least initially, before it becomes something more sexual]]. This works primarily because they're forced together by circumstance, as they have very little in common.
* ''Manga/InsideMari'': High schooler Yori and college student Isao befriend each other, when Isao ends up [[GrandTheftMe in the body of]] Yori's crush, Mari. [[spoiler:Later subverted when it's revealed that Mari has a SplitPersonality rather than there being a body-swap.]]
* ''Anime/Jewelpet2009'': Keigo Tatewaki (early 20's) with Rinko and her friends (14).
* ''Manga/JoJosBizarreAdventure'':
** Joseph Joestar has been on both ends of that trope:
*** In ''[[Manga/JoJosBizarreAdventureBattleTendency Battle Tendency]]'', he's a 18-year old delinquent who's close with the elderly Robert E. O. Speedwagon, his HonoraryUncle.
*** In ''[[Manga/JoJosBizarreAdventureStardustCrusaders Stardust Crusaders]]'', he's [[TheLeader the 68-year old leader]] of a team made up of teenagers (Joseph's grandson Jotaro Kujo, Noriaki Kakyoin), people in their [=20s=] (Jean-Pierre Polnareff, Muhammad Avdol) and a dog (Iggy) and is very close friends with all of them.
*** In ''[[Manga/JoJosBizarreAdventureDiamondIsUnbreakable Diamond is Unbreakable]]'', he's 78 years old. This doesn't prevents him from being one of the few people the 20-year old [[{{Jerkass}} Rohan Kishibe]] openly likes, gets along with and respects.
** In the tie-in game ''VideoGame/JoJosBizarreAdventureHeritageForTheFuture'', the middle-aged Hol Horse has a VillainousFriendship with the young boy Boingo. It later carries over to the series itself with ''Manga/JoJosBizarreAdventureCrazyDiamondsDemonicHeartbreak'', with Hol Horse striking up friendships with the teenaged Josuke Higashikata, as well as with Boingo's young adult brother, Oingo.
** In ''[[Manga/JoJosBizarreAdventureGoldenWind Golden Wind]]'', the 20-year old Bruno Bucciarati is friends with the AffablyEvil CoolOldGuy Pericolo and is noticeably affected by the latter's suicide.
** ''[[Manga/JoJosBizarreAdventureStoneOcean Stone Ocean]]'''s main cast has the 39-year old Weather Report and the 40-year old Jotaro Kujo being close with Jolyne Cujoh (Jotaro's estranged daughter), Ermes Costello, Emporio Alnino, F.F., and Narciso Anasui, all of whom are in their [=20s=] at most (with the youngest, Emporio, being 11, aside from F.F. [[ItMakesSenseInContext being a plankton colony possessing a young girl's corpse]]).
** Lucy Steel has also been on both ends of the trope:
*** In ''[[Manga/JoJosBizarreAdventureSteelBallRun Steel Ball Run]]'', she's a 14-year old girl married with the 51-year old Stephen Steel, but their marriage is a sham to protect Lucy from TheMafia and the true nature of their relationship is actually this trope. While there's nothing romantic in their relationship, they're still much closer to each other than the average friendship. Part of Lucy's motives to help the heroes is to rescue her friend and husband.
*** In ''[[Manga/JoJosBizarreAdventureJoJolion JoJolion]]'', the now 65-year old Lucy befriends the 17-year old Joseph "Fumi" Joestar, and takes him under her wing when he is trapped in the US during [[UsefulNotes/WorldWarTwo WW 2]]. He becomes her assistant and looks after her in the three last years of her life.
* ''Manga/KaijuNumber8'': 32-year-old Kafka Hibino's closest friends and {{Secret Keeper}}s, Reno Ichikawa and Kikoru Shinomiya, are a good 10+ years younger than him. Even around the entire group of new recruits, he's still the oldest among them, yet he gets along well with all of them.
* ''Anime/KikisDeliveryService'': Kiki befriends [[TheHecateSisters three women]], all of different ages. There was the pregnant baker lady, the teenaged artist and an elderly woman.
* ''Manga/KotaroLivesAlone'': Kotaro, the 4-year-old protagonist, becomses good friends with his neighbor, a young adult named Shin Karino.
* ''Kodomo no Jikan'': Aoki-sensei (22) and the three girls (10 each) act like this from time to time. Kuro (10) and Shirai-sensei are an even better example.
* In ''Anime/KurageNoShokudo'', Youtarou forms two with Arashi, the current owner of the Jellyfish Diner, and Natsuko, a close friend of Arashi's who delivers fresh produce to him.
* ''Franchise/LyricalNanoha'':
** Fate and Signum, who first became friends back when Fate was just 9 while Signum... looked and acted to be around 19 but is actually [[ReallySevenHundredYearsOld a few hundred years old]].
** Vita likes hanging out with senior citizens and looks like she's 6, but she's just as old as Signum.
* ''Manga/MagiLabyrinthOfMagic'': there's Aladdin (10) with his numerous friends and allies: Alibaba (17), Morgiana (14), Sinbad (29), Yamraiha (23), Ugo (originally 62 but became ageless), Sphintus (17), Kouha (18) and Yunan (unknown).
* ''Manga/MissKobayashisDragonMaid'':
** Kobayashi (25) and Georgie (somewhere in her teens) instantly become "comrades" over their shared love of maids when they met.
** Shouta (10) gets along really well with Takiya, considering him to be a cool adult.
** Saikawa becomes friends with Ilulu in chapter 45, who (discounting lifespan differences) is about twice her age.
** The sixth ''Mini Dragon'' short has Fafnir go to a guild meetup for an MMO he plays. Discounting [[ReallySevenHundredYearsOld Fafnir himself]], the oldest person present is a middle aged man and the youngest is a woman in her late teens/early twenties.
* Thirty-years-old Satoko Tawada befriends a 12-year-old Mashuu Hayami in ''Manga/MyBoy''.
* In ''Literature/MyNextLifeAsAVillainessAllRoutesLeadToDoom'', a young gardener was hired by an equally young duke and they became fast friends. When the duke died the gardener was heartbroken and simply sat waiting to die so he could see his friend again. However, eight year old Katarina got him out of his funk by constantly hanging around him borrowing tools and making toys together until he eventually realized he was glad to be alive again. He still looks forward to seeing his old friend again, but now he wants to tell his friend all about his granddaughter.
* ''Manga/{{Naruto}}'':
** Naruto and Killer Bee, with the former being a teenager and the latter in his mid-thirties.
** There's also [[VillainousFriendship Itachi Uchiha and Kisame Hoshigaki.]] Itachi met Kisame while he was in his early teens and Kisame was in his mid twenties, and yet, they get along very well. Especially for Akatsuki partners, who kind of have a reputation for bickering. Even the guy whose partner is ''himself''.
** Most of the jounin sensei become this with their students, when said students rank up. For example, take Naruto and Kakashi (respectively 16 and 31) or Shikamaru and Asuma (16 and 31).
** In ''Manga/NarutoGaiden'', [[spoiler:Naruto, who is in his early 30's,]] strikes one with Sarada [[spoiler:Uchiha]] and to a lesser degree Chōchō [[spoiler:Akimichi]], two girls who were both 11 years old at the time.
* ''Manga/NegimaMagisterNegiMagi'':
** Negi (10) and Takahata (mid 30's). Kind of makes sense as Takahata was a friend of Negi's father Nagi.
** Within the [[BadassCrew Ala Rubra]], Eishun is at least 10 years older than Nagi, and Albireo is implied to be even older than that. Jack Rakan is also probably at least a decade older than Nagi. And Takahata was about Negi's age back then. The only one within his same age range was [[spoiler:Kurt Godel]], who was no older than 14.
** Chisame (14 as much) and Jack Rakan also seem to have a bit of an OddFriendship going, as well, especially judging by [[spoiler:her reaction to his death.]] Not to mention Chisame's seeming addiction to age-changing pills to make her a loli further emphasizes this.
* ''Anime/NeonGenesisEvangelion'': Misato Katsuragi (29) and Shinji Ikari (14). This is one of the show's many deconstructions, as while they get along pretty well, Misato bounces from Shinji's commanding officer at NERV to a CoolBigSis at home on a near-daily basis, which keeps them from truly being able to relate to each other in a way that would be mutually beneficial. Things are clouded even further by the ambiguity of exactly what Misato feels for Shinji and both of them having massive emotional and psychological issues that prevent them from being able to meaningfully help each other with their respective problems.
* ''Manga/OnePiece''
** Several of Luffy's TrueCompanions. Up until the Grand Line, all of the crew were in their late teens. Then came Chopper (15), Nico Robin (28), Franky (34), and Brook (88). Post-timeskip adds Jinbe, who's 46 by that point.
** Also Luffy's friendship with Shanks.
** Let's not forget Mr. 2, who is very keen on making speeches about his friendship with the Straw Hat Pirates and was eventually revealed [[AllThereInTheManual in a 2019 databook release]] to be 30 when introduced.
* ''Manga/OuranHighSchoolHostClub'': Eclaire Tonerre (16-17) and [[spoiler:Tamaki]]'s mother (most likely in her fourties).
* ''Manga/OutlawStar'': Gene Starwind (aged about 20) and Jim Hawking (aged 11).
* ''Manga/PandoraHearts'': Any of Break's friendships count as this as although he doesn't look it he's nearly forty. His closest friends are Reim (26) and Sharon (23, although she looks 13) they've been friends since he was 24.
* ''Anime/PokemonTheSeries'': Professor Oak (about 50) and Ash (10 [[NotAllowedToGrowUp for the past 26 years or so]]) are fairly close even though the former taught Ash's mother in school. Possibly averted in that, at least on Oak's end, [[Anime/Pokemon4Ever he first met Ash when he was the same age]] due to some accidental TimeTravel.
* ''Anime/PowerStone'': Ayame Yumatara (14) becomes good friends with Apollus and Pride Falcon (both late middle-aged) over the course of their journey to find the Power Stones, to the point where [[TakingTheBullet she's willing to protect them by taking a powerful blast]] from a transformed Valgas.
* ''Anime/RakugoTennyoOyui'': Suzu (12) and Akira (somewhere in her 20s). Suzu spends the great majority of the series hanging around high school students and old famous people from Japanese history. If it weren't for the tanuki, Ponta, she'd be the only person of her age around.
* ''Manga/RurouniKenshin'' in general. Main protagonist Kenshin is, unusually for a shounen action series, all of 28 years old. He was fighting in the last war when most of the other characters were children.
** Sagara Sanosuke is 19, yet they gamble, drink, and occasionally swap war stories (from the same war, no less).
** Kenshin and 17-year-old Kaoru even more so. [[spoiler:They eventually get married.]]
** More [[VitriolicBestBuds vitriolic]], but also quite loyal: Sanosuke and 10-year-old Yahiko.
* ''Manga/SailorMoon''
** The no-more-than-eight Chibi-Usa is good friends with Setsuna, who is at least in her late teens, but more likely early-to-mid twenties. Then throw in the fact that the Setsuna Chibi-Usa is friends with originally is the thousand-year-old (AND reincarnated) Sailor Pluto, and the gap is a bit bigger. In the manga, Chibi-Usa herself is over nine hundred but looks like a child, and even then Setsuna is significantly older than her.
** Rei Hino (14) and Kaidou-san (early/mid 20's) in the manga. [[spoiler:He actually was Rei's first love, but he married a girl his age and it didn't go beyond a kiss.]]
* ''Anime/Persona4TheAnimation'': Nanako Doujima (6) and all of her cousin [[TheHero Yuu's]] friends (around 15-16), but specially 15-year-old Naoto. [[spoiler:We don't know how strictly old Teddie is, but his human form has the looks of a 15-year-old boy.]]
* ''Manga/{{Saiyuki}} Ibun'': Toudai (who will be known as the Goudai Sanzo) and the youkai Tenkai who would inherit the Maten Sutra before Koumyou Sanzo. Played with, as physically, Toudai appears much older than Tenkai who looks like a young child. But as a youkai, Tenkai could be easily be years older than Toudai while retaining his youthful appearance.
* ''Manga/TheSevenDeadlySins'': princess Elizabeth (16) is friends with the Seven Deadly Sins, all of which are older than her: Ban is around 40, Meliodas is at least 3000 and Diane and King are over 700. Actually any friendship the Sins have outside the group counts. And in the group itself, since there is a huge gap between them (Ban and Meliodas, King befriended [[spoiler:Diane]] when she was a child and he was an adult and ruler...).
** King Bartha too. Aside of Meliodas he befriended Threader and Arthur when they were children.
* ''Anime/{{Simoun}}'': The deep and mutual bond between sixteen-year-old Yun and TimeAbyss Onashia, possibly the ultimate example in terms of actual age difference.
* ''Anime/TheSnowQueen2005'': Gerda (eleven) and Ragi (middle-aged) become friends. There are some shades of ParentalSubstitute.
* ''Manga/TsubasaReservoirChronicle'': Kurogane (mid-twenties), Syaoran, Sakura (teenagers), and Fai might count as this.
** Fai would definitely qualify as this with just about ''everybody''. [[Manga/XxxHolic Yuuko]] mentions in Acid Tokyo that he has already lived many times Kurogane's lifespan. In other words he is not exactly in his early twenties anymore, [[OlderThanTheyLook no matter how young he looks.]] In fact, he is most likely closer to [[Really700YearsOld Yuuko]]'s age than most.
* ''Anime/TheVisionOfEscaflowne'': [[spoiler:Selena Schezar/Dilandau Albatou (around 6 years old at first, later 15)]] and Jajuka (age unknown, but presumably in his twenties).
* ''Manga/WanderingSon'': Nitori and Takatsuki both make friends with two 20 to 30 something year olds named Yuki and Shiina when they were in elementary school. Takatsuki actually met Yuki when she was ([[TheGadfly non-seriously]]) flirting with him one day. It's implied Yuki recognized Takatsuki was also UsefulNotes/{{transgender}} and decided to toy with him. Despite Yuki being MistakenForPedophile once (by Shiina no less) she's otherwise presented as a CoolBigSis.
* Yuzuriha Nekoi (14) and Shiyuu Kusanagi (about 40) in ''Manga/{{X1999}}''. The girl is in love with the man, but it's implied that he cannot be anything more than friends with her due to their age difference and squick factor. [[spoiler:[[MayDecemberRomance They get together in the anime, though]].]]
** An example from the same series is Subaru and Seishirou. It's not as obvious in ''X1999'' where both are clearly adults, but in the semi-prequel ''Manga/TokyoBabylon'' the age gap is much more visible, Seishirou being 25 while Subaru is only 16. Then Subaru falls in love with Seishirou.
** Also, [[spoiler:Kotori]] (high school student, around 16) and [[spoiler:Kakyou]] (in his mid-to-late 20's). The second goes as far as [[spoiler:possessing her body briefly when she dies to take her horrifying physical pain into himself, and then he says goodbye to her as she goes to Heaven, becoming the depositary of her last words.]]
** For that matter, this is the bond that Karen (20-something HookerWithAHeartOfGold) and Seiichirou (30-something manga editor) strike with the younger Dragons of Heaven. (High school age, or in the aforementioned Yuzuriha's case, middle-school age.)
* ''Manga/XxxHOLiC'': Watanuki (about 16) and Yuko (in her late 20's [[spoiler:or so it seems]]), and Watanuki and Haruka.
* Yugi and his friends in ''Anime/YuGiOh'' (all around 16) with Pharaoh Yami/[[spoiler:Atem]] ([[{{Reincarnation}} over 3,000]]).
* ''Anime/YuriOnIce'':
** Yuri Plisetsky (15) and Yuko Nishigori (25) strike up a friendship in Episode 3. Yuko helps Yurio train for the Hot Springs on Ice competition, and she even texts Yurio after he's gone back to Russia in Episode 4. In Episode 11, when Yurio thinks of all the people he's met who have influenced his feelings of ''[[TheFourLoves agape]]'', Yuko is one of them.
** Mari Katsuki (30) and Minako Okukawa (somewhere in her fifties) are good friends even though Minako is stated by WordOfGod to be older than Mari's mother. They travel together to Barcelona to watch the Grand Prix Finals.
[[/folder]]

[[folder:Asian Animation]]
* In ''Animation/PleasantGoatAndBigBigWolf'', the main group of {{True Companion|s}} goats consists entirely of school-aged kids, with the sole exception of the elderly Mr. Slowy who often [[MrExposition provides important exposition]] to help them escape from the wolves or solve some other problem.
[[/folder]]

[[folder:Audio Plays]]
* Singing ClubPresident Mitsuki Akika and their twentysomething teacher Washiho Usuki from ''AudioPlay/ExitTunesPresentsACTORS'' have one. They're even on FirstNameBasis with each other...well, at least when there's no one else around.
[[/folder]]

[[folder:Comic Books]]
* ''ComicBook/{{Asterix}}'': Asterix's closest friend besides Obelix is the druid Getafix, who had his long white beard when all the rest of the cast (save Geriatrix) were children.
* ''ComicBook/{{Batman}}'':
** The Caped Crusader has five ComicBook/{{Robin}}s and three ComicBook/{{Batgirl}}s, though four of the Robins and one of the Batgirls ended up his children, and the younger Batgirls report more to and are better friends with Barbara Gordon than Bruce.
** Tim Drake was friends with the much older Harold Allnut, who is Batman's mute in house mechanic since they both like developing new gadgets. He bitterly brings up Harold's murder when Bruce sent him to ask another genius to help build a new Batmobile, angry that Harold is never mentioned following his death.
%% Zero context* ''ComicBook/GreenArrow'': Olliver Queen has this relationship with, Mia "Speedy" Dearden.
* ''ComicBook/JohnnyTheHomicidalManiac'': The relationship between Johnny and Squee is something like this, with Johnny regarding Squee as a friend/little brother figure. It's entirely one-sided however, as Squee doesn't feel anything other than sheer terror towards him, and with [[AxCrazy VERY good reason.]]
* ''ComicBook/KingsInDisguise'': In the excellent but very grim Creator/DarkHorseComics series involving hobos in the Great Depression, the main character is a young boy who ends up teaming up with a much older man while searching for his father. There's nothing sinister at all about their friendship, but many other hobos traveling with young boys ''are'' in ''[[{{Squick}} exactly]]'' that sort of relationship, and they assume that these two are as well. That's not even mentioning the incredibly creepy old guy who tries to assault the protagonist at one point.
* ''ComicBook/LenoreTheCuteLittleDeadGirl'': Lenore and Ragamuffin is one of the most extreme cases. Biologically, Lenore is 10 years old and Ragamuffin is between 20 and 30 years old. The thing is that Lenore [[UndeadChild has been 10 for 100 years]] and Ragamuffin has been 20-30 for 400 years. So they are like 4 generations apart and Lenore [[CreepyChild is still the one who manipulates him like he is her toy]]... [[SealedEvilInACan which he is, practically, since he is trapped in a small cotton doll]]. And even when he transforms into his old vampire self, he still follows her like a devoted [[MistakenForServant servant]]... ahem... friend.
* ''ComicBook/MyLittlePonyMicroSeries'': Their age difference is never specifically mentioned, but its clear that Twilight and Jade learn to appreciate each other across a generational gap. Jade and Princess Celestia are also old friends, and Celestia is at least a thousand years old.
* ''ComicBook/{{Superman}}'': Superman's relationship with ComicBook/{{Superboy}} (the Conner Kent/Kon-El version) and ComicBook/{{Supergirl}} is something like this. Although they're family -being his clone and his cousin-, Clark generally lets them have their own lives but remains close with them regardless.
* ''ComicBook/SweetTooth'': The main relationship is the friendship between Gus and Jeppard. Gus is 9, while Jeppard looks at least 40.
* ''Franchise/{{Tintin}}'': Tintin and Captain Haddock. They fall in together during the derring do of ''The Crab With the Golden Claws'' and are constant companions from then on. It's difficult to determine when Tintin moves in with Haddock and Professor Calculus but it seems to be some time after the Moon adventure. The sheer oddness of their relationship has led to many snide remarks and speculation down the years, not least because neither are interested in women (the Captain's plain terrified), but theirs is a very sweet and lasting friendship where they continually lay down their lives for each other.
* ''ComicBook/WerewolfByNight'': In volume 1, 19-year-old Jack's best friend is Buck, a writer in his 40s. Jack occasionally wonders if Buck isn't a [[ParentalSubstitute surrogate father]] to him, but then comes to the conclusion that, no, he simply is a very good friend. Later he grows to be best friends with Michael ComicBook/{{Morbius}}, who was already an M.D. with at least one [=PhD=] and a Nobel prize under his belt before Jack had even turned 18.
* ''ComicBook/WonderWoman'':
** ''ComicBook/WonderWoman1942'': A couple of the Holliday Girls, who are a paramilitary group made up of young adults, are friends with a bunch of children who like to play on the streets of Washington D.C. which means that the kids will come tell them when there's suspicous activity or one of their friends has gone missing.
** ''ComicBook/WonderWoman1987'': The teenaged ComicBook/WonderGirl (Cassie) becomes close friends the young adults ComicBook/{{Artemis}} and ContinuitySnarl/DonnaTroy as well as the slightly older Diana.
** ''ComicBook/WonderWomanRebirth'': The KidHero Peony [=McGill=]/Star Blossom jumps at the chance to befriend Wonder Woman.
* ''ComicBook/XMen'':
** ComicBook/{{Wolverine}} and every teenage girl to join the X-Men. In particular Jubilee in the 80s-90s, ComicBook/KittyPryde and Armor. In fact, he appears to get along with teenage girls better than any other type of person.
*** Lampshaded in an old Wolverine issue when he is asked, "do you wonder, why this need for adolescent girls?" - to which Jubilee replies "coz we don't screw his heart and backstab him after like you [adult] cows always do".
** ComicBook/{{X 23}} has one with Gambit in her series. It's not as pronounced as there's only a decade between them at most, but X-23's vulnerability is presented as a [[{{Pun}} sharp]] counterpoint to Gambit's street smarts and maturity.
** X-23's little sister Gabby has a surprisingly sweet friendship with fellow CloudCuckoolander ComicBook/{{Deadpool}}.
** [[Characters/MarvelComicsCyclops Cyclops]] is close to the other founding members of the {{ComicBook/Champions|MarvelComics}}. His younger self was part of their team when he came to the present Marvel universe, and when he went back to his place in time the adult Scott gained all those memories.
** Kieron Gillen's ''ComicBook/UncannyXMen'' run depicted Hope and Namor as this. Hope's a 16 year old {{Child Soldier|s}} and the messiah of the mutant race who grew up in a BadFuture, Namor is an OlderThanHeLooks Atlantian king who's been around and active since [=WW2=]; together they trade snark when paired up on a mission and connect as friends, something both of them rarely do with anyone else.
* ''ComicBook/YokoTsuno'': Yoko (early 20's) and Aoki (60/70's) in ''Daughter of the Winds''. [[spoiler: It ends in tears when Aoki, an ex-war veteran, pulls an HeroicSacrifice for her sake.]]
* ''ComicBookŻyjesz'': In [[PolishMedia Polish graphic novel]] "Żyjesz?" ("Alive?") the nameless heroine of the book is in her 20’s, while the boy she befriends during her adventures is about six-seven years old. They get along pretty well, enjoy each other company and there isn't a single occasion where they aren't trying to save each other (the entire story line is more-or-less SurvivalHorror the comic book).
[[/folder]]

[[folder:Comic Strips]]
* The five-year-old titular protagonist of ''ComicStrip/DennisTheMenaceUS'' tends to be on his elderly neighbor Mr. Wilson's good side whenever the latter is friendly.
* The titular character of the British comic strip ''ComicStrip/RupertBear'' and its AnimatedAdaptation ''WesternAnimation/{{Rupert}}'' is a young boy, but quite a few of his closest friends are adults, the most notable ones being the Professor, the Wise Old Goat, and Constable Growler.
[[/folder]]

[[folder:Eastern Animation]]
* All nine main cast members of ''Animation/KikoRiki'' are friends of different ages. It can be inferred from their manner of speech, interests and mannerisms that 2 are seniors (Carlin and Olga), 3 are middle-aged (Dokko, Pin and Barry) and 4 are youngsters (Krash and Chiko are kids, Rosa and Wally are teenagers).
[[/folder]]

[[folder:Fan Works]]
* ''Fanfic/TheBoltChronicles'': Malcolm, the actor in his 60s who plays Dr. Calico, and teenager Penny remain good friends even after she's quit the show. They are described as [[OlderIsBetter maintaining correspondence via letter]] and Penny serves as a bridesmaid to Malcolm's granddaughter in "The Wedding Reception," while in "The Rings," he walks Penny down the aisle at her own wedding, substituting for her [[DisappearedDad absent father]].
* ''Fanfic/BurningSecret'': Lincoln (a preteen boy) and Kirby the limo driver end up making friends.
%%* ''[[http://web.archive.org/web/20120423151803/http://www.fanfiction.net/s/6804758/1/A_Cup_of_Kindness A Cup of Kindness]]'' has another example. %%No context
* In ''Fanfic/EverydayCrazinessInPontypandy'', due to the lack of people her age around town, 18 year old Gabby's closest friends are 29 year old Elvis and 34 year old Bronwyn. She also has an OddFriendship with 8 year old Norman.
* In ''Fanfic/GalPals'', Lincoln forms a friendship between the titular Gal Pals, with half of them being teenagers (Carol, Becky, Whitney and Dana).
* ''Fanfic/GettingBackOnYourHooves'' has Trixie form one with the Cutie Mark Crusaders after she saves them from a Ropen in the Everfree Forest (though Sweetie Belle already liked her before then).
* In ''Fanfic/GhoulDetectiveSeries'', Ken Kaneki befriended Kuroto Kai when he was a child and idolizes him. [[spoiler:Sadly, Kai died two years later. Even their last conversation is a nod to Elena and Rei's last conversation.]]
* [[AxCrazy Flippy]] and [[{{Moe}} Flaky]] from the ''WebAnimation/HappyTreeFriends'' in ''a lot'' of fancomics, fanart and stories, especially their anime versions. Bonus added with the WifeHusbandry that happens later.
* Lots of ''Literature/TheLordOfTheRings'' fanfiction portrays [[ReallySevenHundredYearsOld Legolas]] befriending Aragorn as a child, such as in ''[[http://www.fanfiction.net/s/2626518/1/Healing-Hope Healing Hope]]''.
** Another concern for their friendship, that many elves remark upon, is the fact that [[WeAreAsMayflies humans have a much shorter lifespan than elves]]. ''[[http://www.fanfiction.net/s/1179397/1/An-Eye-For-An-Eye An Eye For An Eye]]'' has one evil elf lord mocking Legolas for becoming close with a human [[MayflyDecemberFriendship since all humans will eventually die]].
* In ''Fanfic/HellsisterTrilogy'', twenty-nine-year-old ComicBook/{{Supergirl}} and her cousin's teen descendant Laurel Kent get along pretty well. Kara was particularly delighted to meet Laurel because her existence meant [[Franchise/{{Superman}} her cousin]] and ComicBook/LoisLane would end up together.
* ''Fanfic/TheParselmouthOfGryffindor'' has one develop between [[spoiler: Ron and Peter Pettigrew.]]
* In the [[BadFuture Dark World]] timeline of the ''Fanfic/PonyPOVSeries'', Twilight forms one with Pinkie's descendant Apple Pie. This is even more so than initially apparent, as one remembers that Twilight is [[ReallySevenHundredYearsOld over a thousand years old]] by this point.
* In ''[[http://www.100megspop2.com/kayasps/main/mikehero.html Scar The Unsung Hero]]'', Scar (who must've been in his 60's in lion years at least considering it takes place after [[WesternAnimation/TheLionKing1994 the movie]]) befriends a teenage boy. What's weird is that he ends up considering him not only an adopted brother but a "big brother".
* ''Fanfic/TheSecondTry'' has one develop between [[spoiler:4 year old Aki]] and 14 year old [[Anime/NeonGenesisEvangelion Rei]]. This is especially interesting because [[spoiler:Aki technically hasn't been born yet when the two meet]]. And because [[spoiler: she is also the child of Asuka and Shinji, therefore she's Rei's ''niece''. Sorta.]]
* TD of ''Fanfic/TheNonBronyverse'' gets along extremely well with children, but he's especially close friends with the CMC.
* In the ''WesternAnimation/GravityFalls'' fic ''Fanfic/HomeIsWhereTheHauntIs'' has one between Mabel and OC Mr. Mason. [[spoiler: It doesn't end well.]]
* ''Fanfic/SpiderNinja'': Happens a lot:
** The Turtles and Petra are friends with April, despite her being roughly twelve years older than them. It's all but stated that she's a [[PlatonicCoParenting second parental figure]] to the teens, with Petra going as far as saying that April's the closest thing they have to a mother.
** Leo strikes up a friendship with Scott Summers/Cyclops and later [[spoiler:former police captain George Stacy]]. The former is in his twenties while the latter is in his forties.
** Raphael has his canon friendship with Casey Jones, who here is twenty-five while Raph is fifteen. Averted with his friendship with Remy LeBeau/Gambit, who is written as a teenager in this fic.
** Donatello becomes friends with [[spoiler:the [[HeelFaceTurn reformed Doctor Octopus]]]], despite him being roughly twice Donnie's age. The same goes for Doctor Connors, who all the teens consider a friend despite his being in his thirties or forties.
** Averted with Mikey. While he considers April, Casey, Connors, and [[spoiler:Doc Ock]] his friends, the only close friendship he forms with anyone is fellow teenager Bobby Drake/Iceman. They bond over a love of skateboarding.
* In the ''Transformers'' fanfiction, ''Fanfic/BlackCrayons'', Annabelle Lennox is about five years old and considers Ironhide to be her best friend.
* In the ''WesternAnimation/FairlyOddparents'' fanfiction, ''Fanfic/NeverHadAFriendLikeMe'', there is [[JerkassGenie Norm]], the 50,000 year old genie, and [[OriginalCharacter Amanda]], the [[ShrinkingViolet 8 year old]] human.
* In ''Fanfic/HopeForTheHeartless'' (a fanfic taking place after ''WesternAnimation/TheBlackCauldron''), [[VillainProtagonist the Horned King]] is an [[ReallySevenHundredYearsOld over one thousand years]] old [[OurLichesAreDifferent lich]], who's {{Resurrected For A|Job}} RedemptionQuest. He gains as his MoralityPet [[PurityPersonified Avalina]], a 14-year-old peasant girl (who turns 15 during the story), though he shows signs of becoming her deceased father's [[ParentalSubstitute replacement]].
* In ''Fanfic/{{Kage}}'', this seems to be forming between the 12-year-old [[WesternAnimation/JackieChanAdventures Jade]] and the nearly 100 years old [[WesternAnimation/{{WITCH}} Raythor]] (who's middle-aged [[WeAreAsMayflies by his species' standards]]).
* In ''Fanfic/TheUltimateEvil'', Valerie Payne, who's 23 years old in the beginning of the fic, forms a sisterly bond with Jade Chan who's about ten years old.
* ''Fanfic/TheNewRecruit'': Matt is 17-18 when he joins the Avengers (all of whom are in or around their thirties). Despite this, they all seem to get along fairly well, with Bruce acting like a mentor figure for Matt.
* In ''Fanfic/BuildYourWingsOnTheWayDown'' Edward becomes friends with Gabby and Aviv Seif, who are regular university students while he's 12. Lampshaded by Aviv, who also points out that Edward is [[ChildSoldiers part of the military.]]
-->'''Aviv''': When you were twelve, you would have been very happy to have seventeen year old friends.
* Due to his abilities, Harry Potter in ''[[https://www.fanfiction.net/s/11364705/11/Barefoot Barefoot]]'' doesn't see Dumbledore as his headmaster but as Albus and the two regularly chat in his office over various things. To a lesser extent, Harry and Tonks who's in her final year of Hogwarts while he's in his first.
* In the ''Manga/OnePiece''/''WesternAnimation/StevenUniverse'' crossover ''Fanfic/AGemInTheRough'', Petrea and Damian (Miss Valentine and Mr. 5 respectively) do not mind that Steven Universe is far younger than they are and truly see him as a good friend. By the same token, Steven, Connie Maheswaran, and Genevieve (Miss Goldenweek) all get along with the older members of the crew quite well. On the other hand, this trope also unnerves Priyanka Maheswaran when she first meets the Straw Hats, but she warms up to them in time.
* ''Fanfic/BlackSky'' has Theodore Nott - freshly out of Hogwarts so in his late teens or early twenties - going undercover in the Vongola Famiglia by becoming [[CoolOldLady Daniela Vongola's]] personal attendant. He comes to see her as a surrogate grandmother while she fondly nicknames him "Accomplice" for his help in pranking the staff. [[spoiler: Their bond was so deep they Harmonized with each other, something possible only when both parties have common ground.]]
* ''Fanfic/FateIngensCor'': the fourteen-years-old Luna Lovegood and her Servant Caster - middle-aged - have a very friendly relationship, with the girl being genuinely curious about his original time period and the Servant happily telling her everything about nature magic and how lucky he was in his marriage.
* In ''Fanfic/{{Eleutherophobia}}'', Eva and Tom bond over being former involuntary hosts and run a support group together. She's old enough to be his mom.
* ''Fanfic/TheBridge'': several, often between the transferred kaiju and the younger Equestrians.
** Between the earth pony filly [[CuteMute Gentle Leaf]] and the 77,000 year old kaiju, [[BrokenAce Anguirus]]; started with them finding each other while lost and Gentle Leaf being endangered spurring Anguirus to launch himself into the fray against several dragons to protect her.
** [[DarkActionGirl Destroyah]] and the Cutiemark Crusaders ''eventually'' work towards this, inspired by Destroyah accidentally saving them from a Timber Wolf pack and being knocked out before she could turn on them. She did go through multiple DefrostingTheIceQueen moments to mellow her out [[spoiler:and after a HeelFaceTurn, allows them to ride on her back.]]
* In ''Fanfic/AmazingFantasy'', the 14-year-old Izuku strikes up a friendship with the 47-year-old Peter Parker when they meet under surprising circumstances.
* ''[[https://archiveofourown.org/works/11522724/chapters/25863345 Held Together By Spiderwebs]]'' centers on teenage Peter Parker befriending late twenties Steve Rogers.
* ''Fanfic/TheDifferentverse'': Young Scootaloo becomes close enough to the other Bearers, all of whom are adults (and one of whom is her aunt), to have a bond of friendship that lets them activate the Elements of Harmony together.
* The main team of the ''Fanfic/AlternateTailSeries'' mostly has young adults ranging from 17 to 19 with Gajeel, Levy, Lyon, and Mira. However, it also has from the much younger Kagura and Carla at 13 and 6 respectivly as well as the 198 years old Pantherlily, who is described as being around middle-age spiritually. [[spoiler: The fact he is also Carla's father helps add to this trope]].
* ''Fanfic/TheLastSon'' has many examples of this trope with the large amount of superheroes, but one of the most prominent examples is Superman with Captain America. The latter is a World War II veteran, while the former grew hearing the latter's stories and aspired to be like him when he decided to become a hero. When the two finally meet each other, they become fast friend over their shared ideals, and remain staunch allies throughout the story.
* ''Fanfic/SonOfTheSannin'' has Shizune and Itachi, who are about ten years apart in age and are shown to have become close friends by the time that the latter is a preteen. It's through this friendship that Shizune met Itachi's cousin [[SparedByTheAdaptation Shisui]], who she would marry and start a family with during the TimeSkip.
* The ''WesternAnimation/PhineasAndFerb'' fanfic ''[[https://m.fanfiction.net/s/11640990/1/ A tale of two inventors: An unlikely friendship]]'' has a high-school age Phineas befriending his science teacher Dr. Heinz Doofenshmirtz.
* ''Fanfic/FateRevelationOnline'': Well, teenage version. To kids, the difference between an eighteen year-old and a twelve year-old is huge, so Asuna sees her friendship with Illya as something like this. Of course, the audience knows that Illya [[OlderThanTheyLook really is eighteen]] (though she [[ManChild enjoys playing up her appearance a bit]]), so she has more in common with her than Asuna realizes. On the other hand, everyone assumes that Illya and Silica are the same age so their friendship makes perfect sense, but in reality Illya is at least six years older.
* In ''Fanfic/TheMouseInTheWalls'', due to Mirabel's BlackSheep status in the village and family and the fact that Ratón lives alone in the wall of a person's house in secret, they are pretty much the only friends they have despite one of them being in the mid-teens and Ratón pushing fifty.
* In ''Fanfic/TheStoryOfApolloDaphneAndLucaAnItalianTragedy'', the teenaged Alberto immediately becomes good friends with the adult woman [[NamedByTheAdaptation Caterina]], Giulia's mother.
* ''Fanfic/LaterTraitor'': As Frazie (a teenage girl) begins to help the kids of Whispering Rock, she develops friendships with them. She's the closet with Lili, as the two become pals and work together to solve the mystery of the missing campers.
* ''Fanfic/WithPearlAndRubyGlowing'': The Palace support group has a mix of people of all ages, so friendships forming between the kids, teens, and adults are common, such as teenager [[WesternAnimation/{{Brave}} Merida]] with adult [[WesternAnimation/TheGreatMouseDetective Basil]].
* ''Fanfic/AMothToAFlame'': Andrias is well over a thousand years older than Marcy, having personally met her ancestors in Newtopia. Unlike canon, he doesn't try and force himself to see her as just a pawn (despite his genuine fondness for her) and as a result they have a VillainousFriendship. They have basically become each other's OnlyFriend after this fic's version of the event of "True Colors".
* ''Fanfic/OniGaSShikuSeries'': Izuku, at eight years old, is already good friends with Detective Tsukauchi, who is twenty nine at the time. At one point Tsukauchi asks Izuku to pretend to be his adopted kid for a bit so he can pretend he has some kind of social life in front of his mother, but both find it incredibly awkward and the mother tells Izuku she's glad her son has friends like him. It goes even further when [[spoiler:Izuku at age ten goes to face the Yamikumo clan on his own, and instead of trying to stop Izuku Tsukauchi [[ScrewTheRulesImDoingWhatsRight ignores all police proceedure to support him]] instead of telling him to stay back because he's a kid. This is in contrast to what the actual parental figures in Izuku's life do, who try to stop him from putting himself in danger.]]
[[/folder]]

[[folder:Films -- Animation]]
* ''WesternAnimation/WreckItRalph'': Vanellope and Ralph. Somewhat murky since, as video game characters, they don't age normally, but Vanellope certainly looks and acts the part of a small child and Ralph is definitely an adult, and he looks like he'd be old enough to be her father. Also, Ralph's game is much older than Vanellope's, so it works on that level as well.
* Hogarth (nine years old) and Dean (early to mid thirties at most) in ''WesternAnimation/TheIronGiant''.
* Carl (an elderly man, and the main protagonist) and Russell (a kid) in ''WesternAnimation/{{Up}}''.
* Jack and North in ''WesternAnimation/RiseOfTheGuardians''. Jack is a little over three hundred years old but North, being Santa Claus, existed even longer. And that is not taking their physical appearances into consideration where Jack is a teenager and North is around his fifties or sixties.
* In ''WesternAnimation/ThePiratesWhoDontDoAnythingAVeggieTalesMovie'', the main protagonist George befriends a princess named Eloise. George is a rather old man and he has children back home who are around Eloise's age. Eloise is eight.
* Alice and Tati from ''WesternAnimation/TheIllusionist2010''. Alice is a teenager, and Tati is at least 60. Doubles as {{Odd Friendship}} because of their language barrier; Tati is French, and Alice can only speak English.
* Toothless and Cloudjumper in ''WesternAnimation/HowToTrainYourDragon2''. Toothless is stated to be Hiccup's age (about 20), while Cloudjumper was an adult when he accidentally left a scar on the newborn Hiccup's chin. The friendship mostly consists of Toothless behaving like a kitten/puppy trying to play with Cloudjumper, only for Cloudjumper to be mildly annoyed and grudgingly playing back. At the end, [[spoiler:Cloudjumper bows down to Toothless, after Toothless has proven himself to be an Alpha]].
* Tintin and Haddock in ''WesternAnimation/TheAdventuresOfTintin2011'', a young adult and a man at least in his late thirties/forties.
* ''WesternAnimation/MaryAndMax'', from the film of the same name, a lonely nine year old girl in Australia and a 44 year old man with UsefulNotes/AspergersSyndrome in New York.
* WesternAnimation/{{Aladdin}} and Genie. The former is in his late teens, and the latter is well over 10,000 years older ([[OlderThanTheyLook though you'd never know it, to look at him]]).
* WesternAnimation/{{Moana}} is a 16-year-old girl, while Maui is a centuries-old demigod.
* In ''WesternAnimation/TheLittlePrince2015'': The Girl, who's 9 years old, and the Aviator, an old man who tells her about his meeting with the Little Prince. This also applies to the Aviator and the Titular Little Prince, since it happened when the aviator was an adult, while the Little Prince was a child.
* ''WesternAnimation/TheBreadwinner'': Eleven-year-old [[SweetPollyOliver Parvana]] becomes friends with the middle-aged Razaq who fought in the war with her Baba. After Razaq asks her to read him a letter that informs him of his wife's death, he asks her to teach him to read and write and pays her more than she thinks is necessary. [[TastesLikeFriendship He even offers her some of his apple]] [[spoiler: and gets her Baba out of prison, even with a bullet in his shoulder]].
* [[Franchise/WinnieThePooh Tigger and Roo]] are often shown to be friends, but their friendship is especially prominent in ''WesternAnimation/TheTiggerMovie''. It's not clear how old Tigger is, or if stuffed animals even age, but he appears to be clearly older than Roo.
* Bill Bluff and Guy Graham in ''WesternAnimation/DougsFirstMovie'' are a villainous example.
* Miguel and Héctor in ''WesternAnimation/{{Coco}}''. Though Héctor died at an age where he is old enough to be Miguel's older brother, they grew up more than a hundred years apart from each other and they become fast friends within a few hours of knowing each other. [[spoiler:It's revealed that Héctor is Miguel's true great-great grandfather.]]
* ''WesternAnimation/TheProphet'': The young Almitra and clearly older Mustafa form a quick friendship upon meeting each other.
* Jesper and the eponymous [[WesternAnimation/Klaus2019 Klaus]].
* ''WesternAnimation/ABugsLife'': Dot is just a child, but is Flik's only real friend initially.
[[/folder]]

[[folder:Films -- Live-Action]]
* ''Film/OurMissBrooks'': Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks, herself, would surely object to the label "Intergenerational Friendship"!
* ''Film/GoodWillHunting'': Will, the isolated, delinquent, genius teenager from the slums of Boston, and Sean, the middle-aged, dissatisfied and lonely community college psychology professor form a relationship that makes up most of the plot.
* ''Film/FindingForrester'' is about a high school student, Jamal, who meets reclusive author Forrester, and the two become friends. This leads to funny moments such as when Forrester tries to act "hip" by speaking slang, leading to the infamous "You're the man now, dog!" phrase.
* ''Film/HomeAlone'' and its sequel involve friendships between the prepubescent Kevin [=McAllister=] and an older stranger who appears creepy at first, but turns out to be nice. Said older stranger also ends up saving Kevin from the Wet Bandits.
** In the [[Film/HomeAlone1 first film]], it's Old Man Marley, who shovels salt onto the sidewalks. Kevin gets sucked into a rumor by his older brother Buzz that Old Man Marley killed his family, which turns out to be untrue. In fact, when Kevin talks to Marley in a church on Christmas Eve, Marley reveals that he's estranged from his son, and Kevin encourages him to give his son a call. In the movie's climax, when the Wet Bandits have Kevin cornered, Marley [[ShovelStrike smacks both of them in the face with a snow shovel]] and rescues Kevin.
** In the [[Film/HomeAlone2LostInNewYork second film]], the Pigeon Lady is a homeless woman who lives above the New York Philharmonic Orchestra's stage in the Lincoln Center. She's lonely because people seem to always forget about her, and Kevin vows to remember her. After making this connection, the Pigeon Lady saves Kevin after the Wet Bandits threaten him with a gun in Central Park. She douses the Wet Bandits in bird seed, causing them to be swarmed by a flock of pigeons, distracting them long enough for Kevin to slip away. The next morning, Kevin gives the Pigeon Lady a Christmas present, cementing the friendship.
* ''Film/LawnDogs'' is about two disaffected outsiders, a 10-year-old girl and a 21-year-old lower-class man, who become unlikely friends after a chance encounter.
* ''Leon'' (aka ''Film/TheProfessional'') involves an assassin who befriends a 12-year-old girl.
* ''Film/TaxiDriver'' is about a man who befriends a 12-year-old girl as well.
* ''Film/TheCityOfLostChildren'' has a 9-year-old girl who befriends an intellectually disabled man whose younger brother was kidnapped.
* ''Film/BeautifulGirls'' has a very young girl (played by Natalie Portman from ''The Professional'') and an older man.
* In the ''Franchise/BackToTheFuture'' trilogy, high school senior Marty [=McFly=] is probably elderly scientist Dr. Emmett Brown's ''only'' friend in town. At least in the movies, ''how'' they met and became friends is not explained. That relationship simply exists before the first movie begins.
** WordOfGod later explained that the friendship started when Marty was around 13-14 years old. After being told for years that Doc Brown was a dangerous, crackpot lunatic, he snuck into Doc's lab to see for himself and instead was fascinated by what he saw in there and thought Doc's inventions were cool. Doc found him and was happy Marty thought he was "cool and accepted him for what he was". Doc then gave Marty a part-time job helping out with experiments, helping in the lab, and feeding Einstein. [[http://www.mentalfloss.com/blogs/archives/97285 Read for yourself here]].
** Later it was established that Doc actually sought Marty out when the timing was right due to his knowledge of their future friendship.
*** Doc Brown had the idea for the flux capacitor (the device that allows time travel) after hitting his head when he fell while hanging a wall clock. He may have fallen due to being distracted by Marty (having traveled from 1985 to 1955) calling him on the phone. Therefore, to preserve the timeline, Doc Brown must become friends with Marty, so Marty will film the testing of the time machine, go back to 1955, and enable the invention of the time machine. Ever wonder why a mad scientist obsessed with time travel and clocks converted one wall of his house into a huge guitar amp? Because he knew it would make Marty want to come over to his house repeatedly. And he had all of it planned out years before Marty was born, based on watching a video of himself describing inventing the time machine and a letter describing its first use, given to him by . . . Marty.
*** It should be noted that in real life Michael J. Fox and Christopher Lloyd are only 23 years apart. Marty was supposed to be a teenager despite Fox being 24 at the time and Doc Brown was supposed to be in his sixties despite Lloyd being 47 at the time. A notable gap, but hardly the 50-ish years of their characters.
* Middle-aged accountant Henry "Mutant" Weston and nine-year-old Eric from ''Film/MrMagoriumsWonderEmporium''. Plus, Mahony and Mr. Magorium himself. Sure, she might be about 20-30, but he claims to be ''243 years old''.
* ''Film/TheFall'' centers upon the relationship between Alexandria (5), a young immigrant with a broken arm, and her reluctant father-figure Roy Walker (unknown -- based on the actor's age, mid-20s), a paralyzed stuntman. Surprisingly, no one ever suspects anything "funny" between them; the fact that he's a paraplegic may be a factor, but even after hospital officials find out that Roy conned Alexandria into stealing him morphine, he's still allowed to see her.
* The film ''Film/ScentOfAWoman'' is about a poor prep school student slowly developing one of these with a blind, medically retired ex Lieutenant Colonel who has hired him as aide.
* ''Film/LostInTranslation'' is about Bill Murray's character and Scarlett Johannson's character striking up a friendship in Japan, in part because they are both in unsatisfying relationships with their spouses. The ending is ambiguous over whether it is a romantic relationship, but it does not ''have'' to be. It's an even bigger gap seeing Johansen was 17 when she was filming it though her character was somewhere in her 20s.
* ''Film/TheManWithoutAFace'' features a disfigured recluse (played by Mel Gibson) who agrees to tutor a troubled young boy over the summer. Their friendship sparks suspicion amongst the town residents. (Of course, in the book... )
* ''Film/AboutABoy''. Will Freeman, a 36-year-old bachelor, and Marcus, an eccentric, introverted, bullied 12-year-old with a suicidal mother end up close, and Marcus benefits and gradually becomes more confident and "normal" as a result of Will's guidance. In keeping with modern concern about such relationships, Marcus's mother initially thinks Will must be a paedophile and has a go at him in public.
%%* Walt and Tao in ''Film/GranTorino''.
%%* Mr. Ibrahim and Momo in ''Film/MonsieurIbrahimEtLesFleursDuCoran''
%%* Franchise/IndianaJones and Short Round in ''Film/IndianaJonesAndTheTempleOfDoom''
* ''Film/TheUltimateGift'' has the rich twenty-something guy befriend the LittlestCancerPatient.
* ''Film/{{Rigoletto}}'', a man who's at least in his forties and probably older, is reluctently befriended by a young girl to whom he ends up giving music lessons. The other kids from her town end up befriending him as well, with some pushing from the young girl. The adults are pretty wary, due in large part because the man is pretty badly disfigured. It all blows up when it appears that Rigoletto attacked a child. [[spoiler: In reality, the child had fallen off a small dam into a river, and Rigoletto jumped in after and rescued it. When he carried the child into the town, all people saw was a monstrous man carying what looked like a dead child. It... Didn't end well.]]
%%* ''Film/UptownGirls'' included one of these.
* ''Film/TheKarateKid'' movies:
** Daniel [=LaRusso=] and Mr. Nariyoshi Miyagi in the first three movies. Miyagi teaches Daniel self-defense, while Daniel helps Miyagi cope with his grief over losing his family and later, the death of his father.
** Miyagi and Julie in ''Film/TheNextKarateKid''.
** It continues in ''Film/TheKarateKid2010'' remake, with Dre and Mr Han. Then Dre calls Mr Han his best friend.
* Buster with Elwood and Mack (and later, Cab), in ''Film/BluesBrothers2000''.
* The beautiful film ''[[http://www.imdb.com/title/tt0098684/ Yaaba]]'' is about two African children befriending a very old woman, an outcast who is accused of being a witch.
* Teenage boy Max Fischer and middle-aged man Herman Blume in ''Film/{{Rushmore}}''.
* In ''Film/FindingNeverland'', James Barrie strikes up a friendship with the Llewelyn-Davies boys despite being old enough to be their father. It helps that James is very much in touch with his inner child and that two of the boys (Peter and George) often act mature beyond their years. And since the movie is loosely based off of the real life friendship between James and the Llewelyn-Davies family, this would be TruthInTelevision.
* ''Film/CrouchingTigerHiddenDragon'': Jen strikes up a sisterly friendship with LadyOfWar Shu Lien, who is at least twice her age.
* ''Franchise/{{Terminator}}'':
** In ''Film/Terminator2JudgmentDay'', John Connor ([[VagueAge 10, or possibly 13]]) and T-800 (ageless, being a robot, but looking like a man in his 40's) develop this kind of dynamic.
** In ''Film/TerminatorSalvation'', Kyle Reese (ca. 16) and Marcus (ca. 35) become not only friends, but real battle brothers.
* In ''Film/{{Push}}'', the 13-year-old Cassie and Nick, who is in his mid-20s, are reluctant partners when they are chased by the Division and the Triads. By the end, though, they develop a friendship. Of course [[FanPreferredCouple shippers]] see something more
* ''Film/TheLordOfTheRings'': The Fellowship, all with varying ages. Gandalf and Legolas were definitely the oldest of the group,[[note]]Gandalf was created by Eru Ilúvatar before the Ainulindalë, which makes him ''older than the world itself''. Or more precisely, over [[https://lotr.fandom.com/wiki/Timeline_of_Arda 37,000 years old]]. He entered Middle-Earth as a Wizard in the year 1000 of the [[https://lotr.fandom.com/wiki/Third_Age Third Age]], that is, 2,018 years before the formation of the Fellowship. Legolas is a bit more complicated: the movie's official guide states that he is 2,931 years old, but this was never stated by Tolkien himself. So fans piece together hints from the book and [[https://askmiddlearth.tumblr.com/post/41313960261/how-old-is-legolas guesstimate]] anything from 200 to 2,000+ years.[[/note]] with Pippin being the youngest and Aragorn's age is stated to be 87. In fact, this even occurs between the Hobbits themselves. Pippin is still in his "tweens", (the age between 20 and 33 when a Hobbit comes of age), when the Fellowship set out from Bag-End. In comparison, Frodo is 51. This continues in ''Film/TheHobbit'' where Gandalf becomes friends with Bilbo (who was fifty-ish). Also, Bilbo with the dwarves, particularly Thorin and Balin, who are both nearing the two hundreds. Even the younger dwarves like Fíli and Kíli are above their seventies.
* In ''Montreal Main'', a photographer in his late 20s becomes best buds with a 12-year-old boy. Whether or not there's some attraction there is ambiguous; Word of God states that the man "doesn't know what he wants".
* Allan Quatermain and Tom Sawyer develop one of these in the film version of ''Film/TheLeagueOfExtraordinaryGentlemen''.
* Henry Travers who plays the heroine's father in ''Film/ShadowOfADoubt'' was about seventy at the time of filming. Hume Cronym, who played his best friend, Herbie, was about thirty. Originally Herbie was supposed to be played by a must older actor but they liked Cronym so much they they cast him. What results is a charming IntergenerationalFriendship.
* ''Film/TwelveAndHolding'' has Gus (unknown age, but probably in his late twenties or older) and Malee, who has a PrecociousCrush on him. While it's entirely platonic on his side, she takes it a bit too far... [[spoiler:eventually culminating in her setting up a romantic candlelight dinner, complete with a robe which she drops to reveal herself to him. Fortunately, Gus doesn't feel the same way, and promptly calls her mother to take her home.]]
* The nature documentary ''Chimpanzee'' observes the developing bond between Oscar a three-month-old orphan and Freddie the troop leader (likely in his twenties or thirties.) This bond is especially noteworthy as while Chimpanzees are considered capable of adopting orphans this was the first time it was captured on film and even rarer seeing as it was an adult male and the alpha male no less.
* ''Film/PaperMoon'' has Moses Pray and the recently-orphaned Addie Loggins bonding in their various con games against suckers.
* In ''Film/SlingBlade'' a grown man and a young boy become close friends.
* Eventually, the father-and-son relationship that existed between [[Franchise/StarWars Obi-Wan Kenobi and Anakin Skywalker]] evolved into a [[HeterosexualLifePartners very close friendship]], despite the sixteen year age gap.
* Other movies: ''On Borrowed Time'', ''Just You and Me, Kid'' and ''Butterfly''
* From ''Film/TheCounterfeiters'', Sally, who is in his forties, and Kolya, who is around 20.
* ''Film/TigerBay'' revolves around the friendship between a SympatheticMurderer and the 11-year-old girl he kidnaps after she witnesses his crime. [[spoiler: Eventually, LoveRedeems and he lets her go]].
* In ''Film/GIJoeRetaliation'' General Joseph Colton develops one with Lady Jaye.
* ''Film/StarTrek2009'': Possibly, with Spock Prime and Jim Kirk, considering Spock Prime is about 155 and Jim is 25.
* In ''Film/SophieSchollTheFinalDays'', the 21-year-old title character strikes up a friendship with her cellmate Else Gebel, who is in her late thirties.
* ''Film/MyFirstMister'': 17-year-old Jennifer becomes friends with 49-year-old Randal.
* ''Film/EverythingMustGo'': Nick Halsey befriends a neighborhood kid named Kenny who he teaches to play baseball and how to make sales.
* ''Film/BadWords'': 40-year-old Guy Trilby is befriended by 10-year-old Chaitanya Chopra.
* Ray and Dave in ''Film/OffTheBlack''. Over forty years separate the two of them, but they bond over baseball and the fear of never accomplishing anything in life.
* ''Film/HaroldAndMaude''. The titular characters - a teenaged boy and a 79 year old woman.
* ''Film/TheHungerGames'': Katniss and Peeta with Haymitch.
* ''Film/ManOnFire'': Creasy starts out as a suicidal alcoholic until he gradually warms up to Pita, the little girl he's been hired to bodyguard. He decides to help her prepare for a swimming competition and sort of becomes a surrogate father to Pita, driving him to go on a [[RoaringRampageOfRevenge rage-driven revenge quest]] after she's kidnapped and apparently killed.
* ''Film/KidDetective2020'': Abe (32) and Caroline (16-17) develop a friendly bond while working on a crime investigation together. This is probably helped by the fact that Abe still has the maturity of a teenager.
* The film ''Film/{{Laggies}}'' focuses on one of these between twenty-eight year old slacker Megan (Creator/KeiraKnightley) and high school girl Annika (Creator/ChloeGraceMoretz).
* In ''Film/TheGarbagePailKidsMovie'', 14-year-old Dodger is shown to be on very good terms with his adult boss Captain Manzini, who is definitely a lot nicer and more considerate to Dodger than the titular Garbage Pail Kids.
* ''Film/{{MrBeans Holiday}}'': Bean causes Stepan, a russian boy to be separated from his father on the way to Cannes. Although (understandably) Stepan is angry with him at first, they quickly strike a friendship as Bean attempts to return Stepan to his father.
* In ''Film/TheNightOfTheGrizzly'', Gypsy Cole, who's about five or six years old, becomes close friends with forty-something store assistant Hank (Creator/JackElam).
* In ''Film/{{Jasminum}}'' Eugenia is stated to be five and Zdrówko is... hmm. Old (the actor was sixty five while filming).
* In ''Film/{{Along With The GodsThe Two Worlds}}'' The grim reaper, Haewonmak, is an adult male, and the assistant Guardian, Deok-choon is an 18 year old girl, though they are both a thousand years old.
* ''Film/{{Jumanji}}'': As a boy in 1969, Alan is good friends with Carl, one of his father's employees. When they meet again 26 years later, Carl (who's now a cop) understandably doesn't recognize him, then freaks out when Alan tells him. Alan uses the opportunity to trick Carl into letting him escape.
* ''Film/KnivesOut'': The elderly Harlan was close friends with his personal nurse, the twentysomething Marta. [[spoiler:So much so that he decided to cut [[BigScrewedUpFamily his family]] out of his will and leave ''everything'' to Marta instead.]]
* Captain Jack Sparrow and Will Turner in the ''Franchise/PiratesOfTheCaribbean'' franchise. Jack is older than Will - Will's father served under Jack during his (first) run as captain of the Black Pearl - but even in the first film, their friendship is clear.
* Many films starring the 1930's child star Creator/JackieCooper were about his friendship with an adult man. Some of these include; ''Film/YoungDonovansKid'', ''Film/TheBowery'', ''Film/LoneCowboy'', ''Film/TreasureIsland1934'', and ''Film/ToughGuy''.
* ''Film/MackintoshAndTJ'' has a middle-aged drifter befriending a fourteen-year-old runaway.
** ''Film/AllMonstersAttack'': lonely kid Ichiro, aged somewhere around 8-10, has a close friendship with his late middle-aged neighbour Shinpei, who often babysits for him.
* ''Film/TheHoliday'': While on vacation in L.A. the 30-something [[Creator/KateWinslet Iris]] befriends [[Creator/EliWallach Arthur Abbott]], a retired screenwriter from the Golden Age of Hollywood. Arthur provides Iris advice on how to get over her ex-boyfriend and rebuild her self esteem. In return, Iris helps Arthur with his physical therapy so he can attend a Screenwriters Guild event honoring his work.
* In ''Film/TheKing'' Falstaff appears to be at least two decades older than Hal; according to the script Hal is 25 and Falstaff is 45 at the beginning of the film, while in the film itself it's mentioned Falstaff fought during the reign of Richard II (who ruled from 1377 to 1399, while Hal was born in 1386 and would've been around 13 when Richard was deposed). The two are close friends, with the older Falstaff often offering advice to young Hal.
* ''Film/TheIntern'' is about the close friendship that develops between the thirtysomething Jules, the CEO of a fashion company, and 60-year-old Ben, the titular intern. Both of them are lonely, Ben due to being a retired widow and Jules due to being extremely overworked, so they fill void in each other's lives.
* ''Film/AQuietPlacePartII'' has Regan, a girl in her early-to-mid teens, and Emmett, a man who looks to be in his forties, as a BadassAndChildDuo who form a close bond during their travels to the island. Emmett, who lost his family and has become a hardbitten cynic ever since, regains his faith in humanity and a purpose due to his relationship with Regan.
* ''Film/MoreThanEver'': Thirtysomething Hélène platonically bonds with the elderly Bent over their shared experiences with disease.
[[/folder]]

[[folder:Literature]]
* ''Literature/FireAndHemlock'': The protagonist befriends a man who she initially thinks is much older than her, but he seems to have been in his twenties when they first met; she later realizes that he isn't that old, it's just that to a child, all adults seem ancient.
* ''Literature/DragonBones'' has a really weird example with 19-year-old Ward befriending Oreg, a ghost-like being who is almost as old as castle Hurog, which means over a thousand years. There are some other instances where mortals befriend supernatural beings, where this trope applies, but the weird thing about Oreg is that he looks 17 or so - younger than Ward. He's also TheWoobie and frequently ''seems'' that age, or younger, too, especially when he's frightened.
* In ''Literature/TheBartimaeusTrilogy'', Bartimaeus is a demon, thousands of years old and was pretty close friends with Ptolemy and, in the end, is pretty close friends with Kitty and especially Nathanael; all three of them are/were in their teens at that time.
* Blanche of ''Literature/TheBlueNosedWitch'', the youngest witch in Scurry 13, is best friends with the much older Josephine.
* In ''Literature/TheTrueConfessionsOfCharlotteDoyle'', Charlotte is 13, while Zachariah is in at least his 60s. It makes sense to Zachariah, though:
-->"I can assure you," he said with a slight smile, "Zachariah can be a fine friend."\\
"And I can assure you," I returned, "that the captain will have made arrangements for my social needs."\\
"Ah, but you and I have so much in common."\\
"I don't think so."\\
"But we do! Miss Doyle is so young! I am so old! Surely there is something similar in that."
%%* Jim and Huck in ''Literature/AdventuresOfHuckleberryFinn''
* In ''Literature/MySweetOrangeTree'', Zeze is 5, while Portuga, the CoolOldGuy he befriends is in his mid-40. Not quite a friendship, but certainly a case of ParentalSubstitute.
* Creator/StephenKing uses this one repeatedly:
** ''Low Men in Yellow Coats'', the first story in ''Literature/HeartsInAtlantis'' (later made into a FilmOfTheBook) is about a young boy who develops a friendship with the much-older psychic Ted Brautigan. The boy's rather self-centered mother harbors strong suspicions about Brautigan's intentions for her son, which figures heavily into his eventual capture by the inhuman creatures hunting for him at the end of the story.
** Jake and Roland in ''Literature/TheDarkTower'' series. Jake is not quite a teen when they first meet, and Roland is well over fifty.
** ''Literature/PetSematary'', with the Crandalls (both eighty-something) and the Creeds (in their 30s, with two young children who also bond with their elderly neighbors). When they first meet, the narration describes Louis Creed's relationship to Jud Crandall by saying "he called this man a friend, as a grown man must do when he finds the man who should have been his father relatively late in life".
** ''[[Literature/DifferentSeasons Apt Pupil]]'' has a thoroughly twisted version with Todd Bowden and "Arthur Denker" (who is actually a former Nazi concentration camp commander named Kurt Dussander).
** The Bill Hodges trilogy (''Literature/MrMercedes'', ''Literature/FindersKeepers'', ''Literature/EndOfWatch'') has a three-sided example with PowerTrio Bill Hodges (late 60s), Holly Gibney (mid-40s), and Jerome Robinson (goes from 17 to 21 during the trilogy).
* Sandor Clegane and Sansa Stark in ''Literature/ASongOfIceAndFire''. Not quite a friendship, but rather a case of EnemyMine.
* The ''Literature/TalesOfDunkAndEgg'' features the friendship between a 19 year old tall Knight and a young boy named Egg, which isn't a great deal of a age gap, [[spoiler:but for the fact that the Knight is a lowly reformed street urchin and the boy is a Prince of the Ruling Family of the Seven Kingdoms.]]
* Many books by Russian author Vladislav Krapivin feature this trope, with friendships between a child and a young adult, or a young adult and an elderly character.
* ''Literature/LandOfOz'': Cap'n Bill and Trot. She's the daughter of his first mate from when he was a sailor, they now wander around Oz together.
* ''Literature/TreasureIsland'': Long John Silver and Jim Hawkins, even more unusual when you consider that they spend at least half the book as antagonists. Silver is almost explicitly a replacement father figure. At least it explains why Jim, whose own father recently died, takes a liking to Silver despite having been warned about a one-legged pirate.
* ''Bless Me, Ultima'': The friendship between Antonio and Ultima (not only old enough to be his grandmother, but also helped his mother birth him) is one of the central points.
* ''Literature/HarryPotter'':
** Harry, a school-age boy, quickly strikes up a lasting friendship with Hagrid, who's in his 60s and is Harry's introduction to MagicalSociety. He becomes a regular visitor to Hagrid's house for tea and conversation throughout the series.
** Harry becomes friendly with the elderly Professors [=McGonagall=] and Dumbledore as he continues to get into heroics disproportionate to his age. They both think highly of him, though while [=McGonagall=] maintains their teacher-student relationship more firmly, Dumbledore more readily [[TheChessmaster makes use of Harry in his schemes]].
** Harry becomes friends with his godfather Sirius Black after discovering their relationship at age 13. It's complicated by the fact that Harry is eager for a family connection and an adult confidant, while Sirius has a tendency to project his relationship with Harry's father onto Harry himself.
** Dumbledore is in his 110s but maintains many friendships outside his age bracket, including the renowned 600-plus-year-old Nicolas Flamel and the 60-something Hagrid. Being a renowned [[TheArchmage archmage]] and a senior staffer at a WizardingSchool allows one to become very well-connected.
* ''Franchise/TolkiensLegendarium'':
** ''Literature/TheHobbit'': 51 year old Bilbo befriends Gandalf, who is older than time itself.
** ''Literature/TheLordOfTheRings'':
*** Bilbo is nearly 80 years older than Frodo, yet they have a very close relationship.
*** Other examples include the several hundred years old Legolas and the 140 year old Gimli, and the friendship bordering on father-son relationship between Merry and King Théoden. However, one of the most prominent examples is the bond that forms between Gandalf (the "grandfather" of the Fellowship) and Pippin (the "baby" of the Fellowship) when they ride off to Minas Tirith together.
*** Frodo is in his fifties whereas Merry and Pippin are still very young; Pippin is still in his Tweens (the age between 20 and 33 when a Hobbit comes of age). The Fellowship ages vary wildly, therefore they all sort of fit this trope.
** In ''Literature/BerenAndLuthien'', Human warrior Beren and Elven King Finrod have a very close friendship and would give their lives for each other (and Finrod actually did). Beren is 33 and Finrod is 2,291 years old, being older than Beren's race, the Sun and the Moon.
** ''Literature/TheFallOfGondolin'': Tuor and Voronwë (who is at least several centuries older), become close friends after meeting each other in Vinyamar, to the point Tuor trusts him to protect his wife Idril during the battle.
* Quite unexpected bonds fitting this trope are found in Conn Iggulden's ''Literature/{{Emperor}}'' series between Caesar/Brutus and Renius, the elderly gladiator who trained them and tried to kill them in their early teens. The bond between Caesar and Renius is founded almost immediately after the older tried to kill the younger, and lasts to the point where [[spoiler: Renius dies trying to protect Caesar during the Battle of Alesia]]. The bond between Brutus and Renius is somewhat shakier at first, with the former vowing to kill the latter for what he did to Caesar. Though after traveling with Renius to Greece, Brutus comes to view him as the father he never knew. It is however unclear if Renius ever really feels any stronger bonds towards Brutus.
** Another such bond in the series is between Caesar and Octavius.
** Julius' friendship with Cabera. Caesar was all of 14 when he first meet Cabera, who was pushing eighty at the time, but is still strong and spry. When Cabera dies in the third book, it is close to twenty years later, though he had spent most of the decade-long campaign in Gaul partially disabled from a stroke suffered after using his quasi-magical healing gift on one of Julius' lieutenants.
* In ''Literature/TheFrogKing'', the main character Harry has a friendship with a homeless girl called Birdie.
* Nearly every kids' novel written by Creator/JohnBellairs features a relationship like this. Usually it is between a smart preteen who doesn't fit in with his/her peers and an eccentric elderly person who treats the kid like an equal, and they face the supernatural menace of the week together. Later on in each series, the kid usually brings in one or two new friends his/her own age who also become fast friends with the old person. [[Literature/TheHouseWithAClockInItsWalls Lewis Barnavelt]] had his Uncle Jonathan and Mrs. Zimmermann, who he introduced to Rose Rita Pottinger. [[Literature/TheCurseOfTheBlueFigurine Johnny Dixon]] had Professor Roderick Childermass, who he introduced to Fergie. [[Literature/TheTreasureOfAlpheusWinterborn Anthony Monday]] became friends with the elderly Ms Eells and her brother Emerson.
* In Creator/DanAbnett's ''Literature/GauntsGhosts'' novel ''Armor of Contempt'', Dalin Criid and Merrt are stuck in a training/punishment brigade and forge a friendship despite Dalin's being a new recruit, just old enough to join, and Merrt's being a battle-hardened soldier from the founding of the regiment. It continues in ''Only In Death''. In ''Blood Pact'', Merrt comes along to give Dalin moral support when he tells Hark about the twin.
* Canadian teen novel ''Jack's Knife'' has a 14-year-old boy who lives with his overprotective mother, and an elderly man who served as a police officer and is also very knowledgeable about survival skills, as friends. The mother doesn't want her son hanging around this CoolOldGuy, and is completely against the relationship, always suspecting the worst.
* A feature in the Haruki Murakami books ''Literature/TheWindUpBirdChronicle'' and ''Literature/DanceDanceDance'', both which feature a thirty-something year old man befriending a young teenage girl.
* In ''Literature/TheDresdenFiles'':
** Harry Dresden and [[CreepyChild the Archive]] develop one of these.
** After ''Proven Guilty'', Harry and Molly are also this trope [[note]]according to WordOfGod, they're twelve years apart[[/note]]. They bond over their shared interest in magic and rebellious teenage years- much to the annoyance of Charity, who worries for her daughter.
* In the ''Literature/WarriorCats'' series apprentices almost always end up being good friends with their mentors. Fireheart also becomes good friends with Yellowfang, who is old enough to be his mother or grandmother; in return, Yellowfang considers Fireheart [[LikeASonToMe the son she wished]] [[TyrantTakesTheHelm Brokenstar was]].
* The effects of [[Really700YearsOld prolong]] in ''Literature/{{Honorverse}}'' pretty much ensure that the age gaps in ''any'' relationship would be quite wider than we are used to.
** Take Horace Harkness and Scotty Tremaine. The former is a grizzled veteran, [[AntiHero brawler and smuggler]] [[SergeantRock of a noncom]], and the latter a 20-year-old EnsignNewbie fresh out of [[MilitaryAcademy Saganami Island]] in the first book. Twenty years and innumerable adventures later Master Chief Warrant Officer [[spoiler:Sir]] Horace Harkness and [[AcePilot Captain]] Prescott Tremaine [[HeterosexualLifePartners are still together]], with [[spoiler:Sir]] Horace Harkness even hacking the Navy personnel files just to be with his younger friend.
** Manticoran Admiral Lady Sonja Hemphill belongs to the generation of the title character's ''parents'' (she's the classmate of Honor's husband Hamish Alexander, who is forty years older than her), while her Havenite counterpart Admiral Shannon Foraker is at least fifteen years youger than Honor, but the ladies nevertheless become [=BFFs=] as soon as they meet, on the grounds of [[BirdsOfAFeather both being such huge]] {{Wrench Wench}}es.
* The [[NoNameGiven un-named]] 20-something protagonist of ''Kokoro'' befriends a much, much older man whom he calls Sensei, as well as Sensei's wife.
* Ted and Colin from ''Literature/TwoWeeksWithTheQueen'', who strike up a friendship over both having to deal with loved ones being seriously ill.
* 14-year-old Blacky is friends with his elderly next-door neighbour Darcy in the books ''Deadly Unna?'' and ''Nukkin Ya''.
* In ''Literature/GreatExpectations'', Pip and Joe, his sister's husband.
* From ''Where The Heart Is'', Novalee, a teenaged girl, meets Sister Husband, a woman at least in her late thirties/forties. We also have Novalee and Lexie, the nurse who took care of Novalee after giving birth to Americus.
* In ''Literature/TheBookThief'', the girl Liesel (ranging from age 12 to 14) becomes friends with a Jewish man Max, who is twice her age.
* ''Literature/BeyondTheWesternSea'' has Nathaniel (17) and Mr. O'Connell (50), also Maura O'Connell (15) and Mr. Drabble (30).
* Sayuri and Mameha in ''Literature/MemoirsOfAGeisha'', who have a sisterly/mentor-like friendship between them.
* In the Tiffany Aching sub-series of ''Literature/{{Discworld}}'', Tiffany and Granny Weatherwax develop something along these lines, though Granny would probably be hard-pressed to admit it.
* While most of the inhabitants of the magical worlds from ''Literature/AliceInWonderland'' and ''Through the Looking Glass and What Alice Found There'' were pretty rude and dismissive of her, the White Knight temporarily befriended Alice, rescuing her from the Black Knight and escorting her to the end of the chess board. Some believe that the White Knight was Lewis Carroll's AuthorAvatar, given his own friendship with Alice Liddell.
* Lawrence Block's detective character Literature/MatthewScudder has a scrappy urban (read: black) 16-20-something kid following him around, and eventually helping him do things that a 60 something white guy can't get done. Matt even gives TJ his rent controlled apartment, in New York!
* In ''Literature/AnneOfGreenGables'', Anne becomes friends with her best friend Diana's Great-Aunt Josephine, Mrs. Allan (the minister's wife), and her teacher Miss Stacy. In the sequel ''Anne of Avonlea'', as a teacher she befriends her pupil Paul Irving, and Miss Lavender, who becomes Paul's stepmother. In ''Anne of Windy Poplars'', she becomes friends with a young girl named Elizabeth, and in ''Anne's House of Dreams'', she becomes friends with Captain Jim (who is in his seventies) and Miss Cornelia, who is fifty.
%%* Most friendships in ''Literature/TheTwilightSaga''.
* In ''Literature/MosesManOfTheMountain'', Moses's two closest friends are his father-in-law Jethro, who is at least twenty years older than him, and his second-in-command and eventual successor Joshua, who is some forty years younger than him.
* ''Literature/AfterTheQuake''. ''Landscape with flatiron''. Junko, a girl past highschool-age and Miyake, a man in his mid-forties.
* In Creator/SusanCooper's ''Literature/KingOfShadows'', 11-year-old actor Nat is transported back in time to 1599, where he forms a loving friendship with 33-year-old William Shakespeare. Nat's father killed himself and Shakespeare's son died at Nat's age, which is why they are drawn to one another.
* In ''Literature/ThereIsAHappyLand'' by Keith Waterhouse, the 10-year-old NamelessNarrator becomes friendly with "Uncle Mad", a homeless, mentally simple adult man (implied to be at least in his thirties or forties.) Becomes crucial to the plot when [[spoiler:Uncle Mad is accused of the murder and (suggested) rape of a local girl, and the narrator helps him escape.]]
* ''Literature/TheBelgariad'', by Creator/DavidEddings:
** Most of Garion's friendships in the series are this, due to the fact that he is a teenager on a quest with a group of people who are all experienced warriors. Special mention should go to his friendship with Durnik (which formed before setting out on the quest, when Garion ''did'' have children his own age to play with) and with Silk (which was noted as being an especially close friendship compared to Garion's other relations).
** Also, in ''Literature/TheElenium'', there is ''Intergenerational Marriage'' between Sparhawk (the middle-aged Pandion knight, and the protagonist) and young queen Ehlana (on ''eighteen'' years old).
* ''Literature/DiarioDeUnZombi'' has Erico (23) and Paula (8).
* ''Literature/{{Mistborn}}'': After joining Kelsier's oddball team of older men (most of them in their 30s at least), Vin (who is only 16) forms friendships with most, if not all of them.
* Also from Creator/BrandonSanderson, in ''Literature/TheStormlightArchive'' Kaladin is about 20, while his second-in-command and friend from Bridge Four, Teft, seems to be at least 40 or even more, with graying hair and beard.
* Valkyrie and almost everyone else in ''Literature/SkulduggeryPleasant''. With the exception of Fletcher, all her friends are 60-400 years older than she is.
* In the ''Franchise/StarTrek'' novel ''[[Literature/StarTrekTyphonPact Paths of Disharmony]]'', Eklanir th'Gahryn reflects on the value of these. In particular, his friendship with his much younger aide ch'Drena is highly important to him.
* The relationship between the captured Russian officer Ivan Zhilin and his master's daughter Dina in Leo Tolstoy's short story ''A Prisoner of the Caucasus''. Though the age difference was never specified, Zhilin was old enough to be married and Dina was stated to be about 13, this impliying a significant one.
* ''Literature/EvaLuna'':
** Melecio (mid 20's) is in two of these: one with a much older woman nicknamed [[MissKitty La Señora]], the other with a 13-year-old Eva. [[spoiler: When Melecio [[UsefulNotes/{{Transgender}} fully transitions and reinvents herself as Mimi]], both friendships stay, and in Eva's case it's even stronger as they live together.]]
** Eva and Elvira, the cook of the first house she worked in, who becomes her unofficial grandmother.
* ''Literature/TheHungerGames'': Haymitch develops this with both Peeta and Katniss.
* ''Literature/{{Momo|1973}}'': Momo is a little kid. Her two best and greatest friends are Beppo, an old and reserved streetsweeper, and Gigi, a lighthearted young man who loves to tell tales.
* ''Literature/{{Papelucho}}'':
** The 8-year-old protagonist strikes one with an old man at least in his 70's, when they're both hospitalised. Papelucho is there after the birth of his little sister Jimena [[spoiler: and being operated on by mistake]], the old man pretty much lives in the hospital since he has no living family. [[spoiler: It turns out the geezer was actually ''loaded'' in cash, and leaves his riches to Papelucho and his family when he dies.]] To a smaller degree, Papelucho also befriends Berenice, the HospitalHottie in her mid 20's who works as the specific caretaker of the old man.
** Papelucho's old friend [[spoiler:once had a much older friend, a rough BigBrotherMentor whom he worked with when he was around Papelucho's age. The older man disappeared all of a sudden, leaving behind a letter in which he promised to return some day and introduce him to his future family, but he never came back. One of the reasons why the older man cares for Papelucho so much is that he believes the kid to be the grandson of his long-lost friend.]]
* In ''Literature/LittleLordFauntleroy'' an old man gets to bond with his estranged grandson.
* Bodger with both Luath and Tao in ''Literature/TheIncredibleJourney'', though he's closer to the cat.
* During Creator/DanAbnett's ''Literature/{{Eisenhorn}}'' trilogy, Eisenhorn develops the sentiment that, had he and Pontius been born at around the same time, and had Pontius not been evil, they would probably have become incredibly good friends.
* Literature/{{Eragon}} and any of his elf friends. In particular, Arya, who's about 80 years older than him.
* The Literature/MalazanBookOfTheFallen can take this to extremes, such as the middleaged/old human Whiskeyjack, who's about 50, striking up a friendships with Anomander Rake, who's a few hundered thousand years old.
* Young Dr Aziz and Adela's friendships with both the elderly Mrs Moore and 45-year-old Cyril Fielding in ''Literature/APassageToIndia''.
%%* In ''Literature/TheLastDragonChronicles'', David and Lucy forge a bond over trying to rescue a squirrel named Conker.
* ''Literature/ThePowerOfFive'': Matt and Richard's friendship could be viewed this way. [[spoiler:[[TearJerker It doesn't end well.]]]]
* The titular, middle-aged Tom of ''[[Literature/UncleTomsCabin Uncle Tom's Cabin]]'' and six-year-old Eva.
* ''Literature/TheThreeMusketeers'': At the beginning of the story, D'Artagnan is 19 and Athos is said to be twice his age. The age gap is explicitly noted in-universe, as well as the father/mentor role played by Athos. Throughout the story arc they become FireForgedFriends and part of a [[BandOfBrothers Band of Brothers]].
* ''Literature/TheRailwaySeries'' has Duke in an intergeneration friendship with both Falcon/Sir Handel and Stuart/Peter Sam, the 2 younger engines even dearly nicknaming him "Granpuff" as a result. Seems to imply a grandfather/grandson relationship going on there. Aww.
* ''Literature/ShadowSong'' revolves around the friendship of Avrum Feldman and Bobo Murphy, who met when they were 68 and 17 respectively. Avrum shares a similar friendship with Bobo's love interest, who was also 17 when she met him.
* ''Literature/WelcomeToNightVale'', the two main characters Diane Crayton and Jackie Fiero develop a friendship. Diane is old enough to lead the Parent Teacher Association, and Jackie Fiero is nineteen years old.
* ''Literature/TheMazeRunner'':
** Jorge gets along well with many people much younger than him in age, including Brenda and Thomas. In the case of Brenda, he might as well be [[ParentalSubstitute a father figure]], as she already lost hers in a horrific manner.
** In ''The Kill Order'', Mark and Trina with Alec and Lana turn into a makeshift family after the Flare took away their family.
* Literature/HerculePoirot is much older than his best friend/sidekick Hastings. Their age gap is not specified, but Poirot was already at a retirement age in ''Literature/TheMysteriousAffairAtStyles'' while Hastings himself was only 30 then. In the final episode of the [[Series/{{Poirot}} TV adaptation]], Hastings tells his daughter that Poirot was something like a father to him.
* In ''Literature/{{Redwall}}'', Methuselah, an elderly mouse, is one of the closest friends of the young hero, Matthias. The former assists the latter in his quest to find the sword of Martin the Warrior.
* In the ''Literature/DeptfordMice'' trilogy, Audrey gradually develops a bond with the ancient Starwife, though at first she could not stand her, thinking her to be a mean old hag. There is a significance to this bond because [[spoiler:Audrey becomes the Starwife's successor after her death.]]
* In ''Literature/BeforeNightFalls'', Reinaldo and Virgilio begin their lifelong friendship aged 23 and 54, respectively.
* ''Literature/TheFourteenthGoldfish'': Ellie becomes closer to her grandfather after he starts living with her and her mother, and starts going to school with Ellie.
* ''Literature/TheLastDogs'': Max, a younger yellow Labrador retriever, is friends with an older black Labrador retriever named Madame Curie. Her urging Max to discover the meaning of the symbol on her collar is what sets Max off on his journey: to find her and help her find the humans.
* ''Literature/{{Power}}'': Teenage Omishto is close friends with her elderly "aunt" Ama, despite the generational gap. This friendship is later brought into question at Ama's trial, when the judge implies that Ama may have been influencing her due to their age differences.
* In ''Literature/FlaviaDeLuce'', the eleven-year-old Flavia has a peculiar, intense, and devoted friendship with Dogger, who has been at war with her father and was then kept around as her father's handyman, chauffeur, gardener, or secretary, whatever his frail mental state allows him to work. Flavia has learned to handle his bouts of PTSD, and she has an enormous respect for Dogger who gives her whatever counsel she needs, watches over her, and offers her understanding when no one of her family does.
* Dr. Erland with Cinder and the Rampion crew in ''Literature/TheLunarChronicles''. Erland is old enough to be the grandfather of most of them ([[spoiler: or father, in one case]]), and yet becomes a trusted member of the team.
** Prince Kai and his father's advisor, Konn Torrin, also clearly have a strong bond, and Kai trusts him more than anyone.
* Father Brown and Flambeau in ''Literature/FatherBrown''. Although [[VagueAge no specific ages are given]], there is a general impression that Flambeau is younger than the little priest.
* ''Literature/AspergerAdventures'': In ''Lisa and the Lacemaker'', Lisa, who seems to be about twelve, befriends Granny May's sister Hannah, who is somewhere in her eighties. It's implied that Hannah has Asperger syndrome as well as Lisa, so they get along well.
* ''Literature/ChocoholicMysteries'': In "Kidnapping Clue", Lee (then a teenager) meets and, after some initial nervousness, becomes friends with Inez Deacon, a retired schoolteacher.
* ''Literature/TheLittlePrince'': The narrator, an adult pilot, forms a deep friendship with the titular Little Prince, who is a little boy.
* ''Literature/BeautifulMusicForUglyChildren'': Eighteen-year-old Gabe's only real friend besides Paige is his next door neighbor John Burrows, an elderly DJ who was the first person in the United States to play Music/ElvisPresley on the radio. John is the only person Gabe knows who's as obsessed with music as he is. He even got Gabe his job as a DJ at KZUK.
[[/folder]]

[[folder:Live-Action TV]]
* ''Series/GameOfThrones'': Between Princess Shireen Baratheon who is 13-15 throughout the series and Ser Davos Seaworth, a grown man. He gives her a toy ship and talks with her, she offers to help him read and visits him when he is imprisoned.
* ''Radio/OurMissBrooks'':
** Miss Brooks' best friend and confidante is her landlady Mrs. Margaret Davis. Mrs. Davis states a few times that she is "sweet sixty" (i.e "The Big Game"). Miss Brooks is hinted to be in her late twenties in several episodes of the program.
** Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks herself would surely object to the label!Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks, herself, would surely object to the label "Intergenerational Friendship"!
* In ''Series/{{Selfie}}'', main characters Eliza and Henry are separated by a generation-their official ages are unspoken (the actors are some 16 years apart), but Eliza is most likely in her mid to late twenties, with Henry being at least ten years older than that. In one episode, she calls him a Baby Boomer, and he points out that he falls squarely within the parameters of Generation X, while Eliza is a Millenial. He expresses distaste with a lot of her generation's traits, and she points out their differing views on sex (which he refers to as "being intimate", she laughs at him for this).
* ''Series/{{Community}}'': The study group consists of three Millennials (Annie, Troy and Abed), three Gen-Xers (Jeff, Britta and Shirley) and one Boomer (Pierce).
* ''Series/BoyMeetsWorld'' has Mr. Feeny who considered the main characters his students his friends. This wasn't as present in the early seasons as Feeny was more of a stern but ReasonableAuthorityFigure, but by the end of the series run the line between teacher and student had blurred considerably. A season 6 episode has Cory and Shawn exploit this using their friendship with Feeny to get him to be lenient with them on a paper they hadn't turned in.
** This is played completely straight with Mr. Turner and Shawn where Turner takes Shawn in after his dad takes off to go after his mom. and the two become friends. Turner himself from the start is portrayed as the cool teacher that tries to relate to his students assigning the students an X-men comic to use as a comparison to the Odyssey.
* The Doctor in ''Series/DoctorWho'' is several centuries older than the majority of his companions. Even Romana, a Time Lady and his equal, was younger by about six hundred years. The friendships (and occasional romances) that he strikes up with his companions form a core element of the series. Initially the age difference between the Doctor and most of his friends was measured in centuries; this later extended to millennia and, as of the end of Series 9, the gap is now measured in ''aeons''.
* Captain Jack Harkness in ''Series/{{Torchwood}}'' is over a century older than the rest of the team [[spoiler:at least at the outset. Three series later, the gap's increased to several ''millennia''.]]
* Sarah Jane Smith in ''Series/TheSarahJaneAdventures'' is well into the CoolOldLady age range. Her closest friends are all teenagers, other than the Doctor, of course, who out-ages her by centuries.
* The study group members on ''{{Series/Community}}'' run the gamut from late teens (Annie, Troy) to mid-thirties (Jeff, Shirley) to late sixties (Pierce).
* ''{{Series/Firefly}}'' has BadassPreacher Shepherd Book becoming unexpectedly good friends with BoisterousBruiser Jayne.
** By the end of ''Film/{{Serenity}}'', Mal and River.
* Gabrielle starts one in ''Series/DesperateHousewives'' when she befriends a lonely neighborhood boy, Eddie, [[spoiler: who later turns out to be a serial murderer]]. The friendship only lasts for one episode, though.
** Also, the housewives and Mrs. [=McLusky=], who is older than them. On the show, friendships between people of different ages are not considered anything special and it is basically taken for granted that that once grown, children become friends with their parents' friends.
* Lex Luthor on ''{{Series/Smallville}}'' started off friends with Clark, supposedly because Clark saved his life. He was around 9 when Clark landed in Smallville, which when Clark was a high school freshman would make him a 21 year old who's best friends with a 14 year old. The DawsonCasting keeps this fairly unnoticeable, as both actors are really in their 30s.
** He started out as the BigBad, but following his own HeelFaceTurn and Lex's FaceHeelTurn, Lionel Luthor did his best to become friends with ''Smallville'''s main cast, despite being somewhere in his fifties, while they were all in their teens. He manages to pull it off pretty well with regards to Clark and Chloe. Hawkman has this with Stargirl, Clark, and Oliver; Perry White has it with Lois.
* ''Series/{{Lost}}'' has [[CoolOldGuy Locke]] form a friendship with 10-year-old Walt that Michael did not like at all. Heck, if you want to get technical, seeing as Locke is the only Flight 815 passenger who is middle-aged (not counting side characters like Rose and Bernard), ''any'' friendship with him and another Lostie is an IntergenerationalFriendship.
* ''Series/StationEleven'': Arthur Leander had a genuine bond with Kirsten, one of the child actresses playing his onstage daughter.
* ''Series/StarTrekDeepSpaceNine''
** The show has a variation on this with the Dax symbiont being old friends with Benjamin Sisko, despite the symbiont being several times his age. It started with this trope applying twice with both the Dax symbiont and the Curzon host being significantly older than Ben, which is why Sisko calls Dax "old man" even when it's in the body of a young woman. This trope applies both ways simultaneously with Jadzia and Ezri as the hosts are much younger than Benjamin, while the symbiont is much older.
** Another intergenerational friendship existed between O'Brien and Bashir, who were in their forties and twenties respectively when the show started. Bashir's naivete and O'Brien's occasional world-weariness meant that the age gap sometimes seemed a lot more.
* ''Series/StarTrekTheNextGeneration''
** "[[Recap/StarTrekTheNextGenerationS5E11HeroWorship Hero Worship]]" involves Data's relationship with a boy of about 10 or 11, who idolizes him for saving his life.
** In "[[Recap/StarTrekTheNextGenerationS2E15PenPals Pen Pals]]", Data becomes "pen pals" with a young alien girl, whose memories they have to erase because of the [[AlienNonInterferenceClause Prime Directive]]. Then later Data becomes friends with another young alien girl, which ends with his memories being erased.
** Wesley Crusher and the rest of the crew. At first, he's around 16, and many of the crew are twice as old as he is, sometimes older.
** Technically, this trope applies to Data's friendships with the crew since chronologically he's not much older than Wesley.
* ''Series/StarTrekVoyager'' has Naomi Wildman, who was born on the ship, and former Borg drone Seven of Nine, who is closer in age to Naomi's mother, forming a strong bond.
* The friendship between Octavius and Vorenus + Pullo in ''Series/{{Rome}}''.
* In ''Series/BuffyTheVampireSlayer'', Giles begins as Buffy's Watcher but a deep friendship develops despite their many differences. This caused him to be sacked for having 'a father's love' for her. It also led evil werewolf catcher Cain to assume they were having a fling and make salacious remarks. They get rather angry at the insinuation.
--> '''Willow''': This is Giles. He's our grown-up friend. Oh! Not like that.
* And of course, used again in ''Series/{{Angel}}''. As a vampire, Angel is several hundred years older than those closest to him. Despite that, he ends up becoming best friends with Cordelia.
* ''Series/ForeverKnight'' is very similar to that with Nick (800yrs old) and Natalie (just over 30)
* ''Series/TrueBlood'', too. Godric (2,000 years old) and Erik (1,000), Erik and Bill (roughly 150) among others.
* Mick and Beth in ''Series/{{Moonlight}}''.
* Duncan and Richie in ''Series/{{Highlander}}: The Series'' and probably Duncan and Methos to a lesser extent.
* ''Series/TheTwilightZone1959'': Ben (well over 1000 years old, appears to be about seventy) and Jenny (probably about nine-ish) in the episode "[[Recap/TheTwilightZone1959S3E25TheFugitive The Fugitive]]".
* Madison and JD on ''Series/HarpersIsland''. Even though it mostly consisted of "hey watch me do bad stuff in front of you."
* Omar and Butchie from ''Series/TheWire'': originally it looks like just a professional relationship, with the semi-retired Butchie as Omar's bank and the go-to man for third parties that want to contact him, but it becomes apparent that they have probably the closest relationship Omar has with ''anyone'' except possibly his grandmother. [[spoiler:Butchie's torture and murder is what brings him out of retirement.]]
* In ''Series/{{ER}}'', Sam's son Alex strikes up a friendship with Dr. Kovac, perhaps trying to get him and his mother together.
** Carol and her teenage lab partner when she's taking pre-med.
* In ''Series/WizardsOfWaverlyPlace'' this is Alex and Mr. Laritate in the third season. Also, Justin and his peers.
* In an episode of ''Series/YesDear'', Greg's 65 year old father has recently retired and gotten into Superman comics. He goes to a comic book convention and runs into his internet buddies, who are all no older than 12.
* Steven Hyde and Leo in ''Series/That70sShow'' are a prime example of this. Aging 60's hippie meets teenage burnout.
* Spencer and Sam on ''Series/ICarly''.
** ALL of Spencer's friendships except T-Bo and, arguably, [[TheGhost Socko]]. This is commented on regularly (and was even an episode premise).
* ''Series/ItsAlwaysSunnyInPhiladelphia'': Frank Reynolds is old enough to be the father of the other main characters ([[NotActuallyHisChild and kind of is in the case of Dennis and Dee]]) but is considered one of the Gang.
* Sikowitz from ''Series/{{Victorious}}'' acts more like a friend than a teacher towards his students in many episodes, as he also helps them with personal problems or even pulls pranks on them
* Goomer and Dice from ''Series/SamAndCat'' have an age difference of 15 years and therefore also qualify. It is even implied Goomer is Dices best friend
** though mentally, Goomer acts much younger than his actual age
* around 16-year-old Max from ''Series/TheThundermans'' states multiple times that around 43-year-old Dr. Colosso is his best friend. Colosso calls him the "evil son he never had"
* One episode of ''Series/{{Being Human|UK}}'' saw Mitchell befriending a boy who was their neighbor, protecting him from bullies and hanging out with him. The boy's mother is initially glad that he is being so nice, but things turn south when she catches the boy watching a vampire snuff film he got from Mitchell (Mitchell offered to loan the boy any of his Laurel and Hardy [=DVDs=] and forgot that he hid the snuff film in one of the cases). Cue accusations and a massive PaedoHunt, which the boy tries desperately to put an end to. [[spoiler:It doesn't end well for anyone.]]
* Blair and [[EthnicMenialLabor housekeeper Dorota]] on ''Series/GossipGirl''.
* In an episode of ''Series/KateAndAllie'', Chip befriends Louis, a mentally handicapped and good-natured homeless man who appears to be the same age as his mother Allie. Kate and Allie initially hear Chip tell about his exploits with Louis and assume that Louis is another child, but later learn his true age when they find him in their house in the middle of the night after Chip invited him in so that he would have a place to sleep. Louis reappears in a few more episodes and his friendship with Chip continues.
* ''Franchise/SuperSentai'' has done this several times. Examples include Nozomu (10-11 years old) and Alata (21 years old, according to WordOfGod) in ''Series/TensouSentaiGoseiger''; and Kou (9) and Lin (18) in ''Series/GoseiSentaiDairanger''. The latter overlaps with MayDecemberRomance since the show's epilogue implies they married or had a romance later on.
* In an episode of ''Series/StepByStep'', we meet the twentysomething Cody's longtime best friend who's a middle aged man.
* On ''Series/TheYoungAndTheRestless'', the rich and elderly Katherine is best friends with the decades younger former stripper Nikki.
* In ''Series/{{Merlin|2008}}'', the elderly physician Gaius is friends with a lot of much younger people, particularly Guinevere. (Merlin himself belongs in the LikeASonToMe category, and he's technically employed by Arthur).
* Walter with Olivia and Astrid in ''Series/{{Fringe}}''.
* Appears on ''Series/TheWestWing'' as the characters are TrueCompanions and their ages span from early twenties to late fifties. The two friendships that stand out are The President and Charlie, and Leo and Josh.
* Zuri and Nana Banana in ''Series/{{Jessie}}'' is about as big of an age gap as you can get. A 7 year old with a woman old enough to be Great-Grandmother when you consider the actual age of both actresses.
* In ''Series/ModernFamily'', Luke (who is 11 years old) becomes friends with the grumpy old neighbor (who apparently fought in World War II).
* ''Series/{{JAG}}'': Harm and his late father's wingman Tom Boone.
* ''Series/{{Arrow}}'':
** Tommy Merlyn and Thea Queen had this, owing to Tommy being best friends with her brother before he went missing; she had something of a crush on him and he acknowledged that she was an attractive young woman, but they remained merely good friends. [[spoiler: After his death, she would find out he was her half-brother, making it HeartwarmingInHindsight....and also a little squicky]].
** On the island, Oliver became good friends with Slade Wilson, a man at least a decade older than him, due to a mutual reliance on one-another. [[WeUsedToBeFriends It unfortunately ends tragically]].
** Oliver seems to have stricken one up with Roy Harper as well, due to Roy's HeroWorship of Oliver's alter-ego. When Roy is given super strength that come with mental issues, Oliver steps in to try and help him with it, and while the two have problems, [[spoiler:Roy becomes the fourth person Oliver intentionally revealed his identity to, and once cured of Mirikuru, eventually becomes his sidekick.]]
** The sister Series ''Series/LegendsOfTomorrow'' has Firestorm's two halves. Dr. Stein is at LEAST twice as old as Jax. And while they do need to physically be around each other every now and then to survive, they both like and willingly talk to/hang out with the other. Jax also ends up having it with some other members of the cast, like Captain Cold.
* ''Series/OneTreeHill'' has several examples, such as Whitey with both Keith and Karen, Chase with Chuck, and Jamie with Quentin, as well as with his [[HonoraryUncle honorary family members]], Brooke, Julian, and Skills.
* ''Series/{{Gotham}}'': When Barbara comes home after a few weeks to find Selina Kyle and Ivy Pepper squatting in her apartment, she just shrugs and starts chatting amicably with them. Later, they're seen helping her pick out a dress, and she in turn helps them with their minimal dating lives.
* [[Literature/{{Pinocchio}} Marco (Gepetto) and Archie (Jiminy Cricket)]] in ''Series/OnceUponATime'', but not in the way they appear. Gepetto is an old man and Jiminy looks like a man in his late thirties[=/=]early forties, but it's later revealed that when they met, Gepetto was a little boy and for reasons too complex to get into here, Jiminy hasn't aged since that day. He's actually several decades older than Gepetto despite looking young enough to be his son.
* In one episode of ''Series/QuantumLeap'', Sam Leaps into Jimmy, an adult with Down's syndrome who lives with his brother's family. Jimmy and his young nephew are best buds and share a set of bunk beds. Also, Sam's own closest friend Al is more than a decade older than him.
* In Korean variety show ''Series/RunningMan'', the main cast have varying ages: from late twenties (Kwang Soo), thirties (Jong Kook, Gary, Ji Hyo, Haha) and forties (Jae Suk, Suk Jin).
* ''Series/TheFlash2014'': There are elements of ParentalSubstitute and LikeASonToMe to varying degrees in each relationship, but Harrison Wells explicitly refers to Barry, Cisco and Caitlin as his closest friends. (It's likely that they're also his only friends, as he has no social life outside of STAR Labs due to being a pariah to most of the city.) All three of them are in their twenties and, although his age is never stated, Harrison is either in his forties or very early fifties. (His actor, Tom Cavanagh, was 50/51 at the start of the series, and is OlderThanHeLooks.)
* In ''Series/{{Oshin}}'', the then-seven year old protagonist's first actual friend was an already adult deserter of the Imperial Japanese Army, Shusaku, who saved her from [[SnowMeansDeath dying in the snow]], let her stay in his hut, and taught her how to write and read. [[spoiler: Unfortunately, Shusaku was eventually caught by the Army and promptly executed for desertion.]]
* ''Series/VeranoAzul'' is about the friendly bonds developed between Chanquete (50/60's), Julia (probably late 30's/early 40's), and a bunch of outsider kids (more or less in the 7 to 14 age range)
* ''Series/TheOA'' has Prairie (28) and Betty (somewhere in her 40s) forming a strong bond with four teenage boys -- Steve, Jesse, French, and Buck -- as Prairie tells them all her life story. Deconstructed because people keep jumping to the conclusion that something inappropriate is going on, being unable to think of a non-creepy reason for grown women to spend so much time with high school students. [[spoiler: Betty is even forced to quit her job over it]].
* ''Series/{{Bewitched}}'': Darrin and his boss Larry Tate, who is at least a decade or two older than Darrin. Darrin usually goes to Larry for marriage advice, since he has far more experience in that field.
* Thelma and Iola in ''Series/MamasFamily''. Iola is about the same age as Thelma's son.
* In ''Series/Supergirl2015'' season 3, Alex (who's [[AllLesbiansWantKids always wanted kids]]) forms a bond with Sam/Reign's teenage daughter Ruby. In the episode "Fanatical", a subplot has Alex trying to help Ruby through her grief while J'Onn is trying to help his father with his illness. After a trip to the arcade goes very wrong, Ruby and the millennia-old Martian are able to talk to each other instead.
* ''Series/Switch1975'': Frank [=MacBride=] is a retired cop in his sixties. His partner Pete Ryan is about 25 years younger, going by the actors' ages. In "Stung from Beyond," the two even go undercover as a father and son.
* ''Series/GoodOmens2019'': Anathema (mid-twenties) and Adam (just barely eleven) take to each other like a house on fire. They meet when he overhears her crying, he approaches her to see what's the matter and if there's anything he can do to help. She tells him there's not, but she clearly appreciates the gesture and invites him inside for a snack. Adam inquires if the rumor that Anathema's a witch are true, and she replies that no, [[DistinctionWithoutADifference she's an occultist]]. She then shares some of her occult magazines with him, which he finds utterly fascinating, and soon, he introduces his other friends to her, too. (They're all allegedly against "witches," but it's pretty clear they all think the idea of a witch living next door is awesome.)
* ''Series/TheTwilightZone1985'':
** In "Paladin of the Lost Hour", there is a more than thirty year age gap between Gaspar and Billy Kinetta but they quickly become very close friends.
** In "Extra Innings", the [[CareerEndingInjury down-and-out baseball player]] Ed Hamner, who is his late 30s, is good friends with his 12-year-old neighbor Paula, a huge baseball fan who idolizes him.
* Intergenerational relationships are a major theme in ''Series/TheNoddyShop''. For instance, the children are friends with Aunt Agatha, the sister of their grandfather Noah.
* Downplayed on ''Series/YoungSheldon''. Sheldon Cooper is a nine-year-old boy in high school and befriends a student named Tam Nguyen. Tam's age is never given, but he'd be at least five years older than Sheldon. Tam also occasionally hangs out with Sheldon's twin sister Missy and their neighbor Billy Sparks, who's the same age as Sheldon and Missy.
* In ''Series/ParksAndRecreation'', April is significantly younger than the rest of the major characters, and started out at the Parks Department as a college intern while the rest of them were mid-career adults (or nearing retirement in the case of Jerry). Lampshaded in a story arc where Ben and April go to DC to work on a congressional campaign, and all the other staffers assume she's his daughter.
* ''Series/TheNeighborhood'': Calvin and Tina Butler are in their fifties. Dave and Gemma Johnson are in their late thirties/early forties, not much older than the Butlers' sons Malcolm and Marty, who are also friends with the Johnsons' ten-year-old son Grover.
* ''Series/{{Devs}}'': Lyndon and Stewart seem to be inseparable while working on the Devs project in spite of Stewart being elderly and Lyndon being 19. Lyndon is even played by a [[CrossCastRole young woman]] to make him seem even younger. An early scene has Stewart grousing that people in Lyndon's generation have no culture.
* ''Series/OnlyMurdersInTheBuilding'': Charles and Oliver are both over forty years older than Mabel, but the three bond over their shared interest in TrueCrime, and their collective suspicion that a suicide that occurred in their apartment building was actually a murder. Mabel snarkily lampshades it, asking Charles "how invested" she should get in them, since he and Oliver are both quite old and she doesn't want to get attached to two men who might die soon for the same reason she wouldn't adopt a twenty-year-old dog. They all become close anyway.
* ''Series/LazyTown'': Sportacus and Stephanie have this, with the former being an adult and the latter being a tween. They met after she contacted him for help and soon bonded thanks to their mutual athleticism and perkiness.
* ''Series/LastOfTheSummerWine'' has several:
** The Trio generally have this sort of rapport with Sid from the Cafe, partly because they always go there and partly because Sid gets bored easily.
** When Tom Simmonite stops hanging out with Truly and Clegg, he befriends Smiler who is his co-worker in Auntie Wainwright's Shop.
* ''Series/QueenSugar'': Ernest Bordelon and Remy Newell, who are appropriately aged to be father and son. Charley is initially surprised when she meets Remy because she expected him to be much older.
* ''Series/TheFullMonty2023'': School caretaker Dave befriends Dean, a 12-year-old student, after he finds the boy has been nicking food from the school kitchen. Dave even stands up for the boy after witnessing him being bullied.
[[/folder]]

[[folder:Music]]
* In "Cory's Coming" by Music/HarryChapin, a young man frequently visits Old John Joseph.
* "Clair" by Gilbert O’Sullivan. He wrote the song about the young daughter of his then-manager, whom he often babysat. It’s actually a lot less creepy than it sounds.
* "Better People" by India Arie. She basically sings that if people would connect with other people older and/or younger than them, the world would be better off.
* [[ItMakesSenseInContext Elizabeth Darcy and Mr. Woodhouse]] in the ''Literature/MrAndMrsDarcyMysteries''.
* An early Music/DavidBowie song "The Little Bombadier" is all about this trope, including the (incorrectly) sinister interpretation of those observing the events.
[[/folder]]

%%[[folder:Myths & Religion]]
%%[[/folder]]

[[folder:Podcasts]]
* ''Podcast/UnwellPodcast'': Dot Harper and Wes.
* ''Podcast/WoodenOvercoats'':
** Georgie's in her early twenties or so, and Mayor Desmond is at least sixty, likely a little older. However, the two have become good friends since she started working as his assistant, to the extent that she stands up for him at his wedding.
** In "Rudyard Takes a Hike," the titular character (about thirty-five) bonds with and becomes protective of the ten-year-old Calliope, because she reminds him of himself when he was a child: [[AllOfTheOtherReindeer isolated and teased]], with an interest in death that others find off-putting. He jumps to her defense a number of times, and after she's eventually accepted by her peers and made troop leader, she invents a badge just to award to Rudyard as a show of her appreciation. At the end of the episode, Calliope also gets on with Rudyard's twin sister Antigone.
[[/folder]]

[[folder:Pro Wrestling]]
* {{Invoked|trope}} with Wrestling/{{CMLL}}'s Torneo Gran Alternativa, which was put in place to cultivate these kinds of friendships by requiring wrestlers of different generations to {{tag|team}}\pareja if they want to enter. Although it also allows [[LegacyCharacter successors and predecessors of a gimmick]] to team up as well.
* Happens often with mentor/student storylines.
* Wrestling/RicFlair and Wrestling/TripleH have a 20 year age difference. Their hanging out together backstage led to the creation of the group, Evolution.
* Wrestling/{{Ivory}} and Wrestling/MollyHolly, who are 16 years apart, but have been close friends since Molly came to the WWF in 2000. They regularly traveled together, did the "Kickin' Ass For Gas" tour in the indies in 2006 (the gimmick was they were trying to earn enough money to get to Wrestling/TrishStratus' wedding) and when Ivory went into the WWE Hall Of Fame in 2018, she chose Molly to give her induction speech.
[[/folder]]

[[folder:Radio]]
* ''Radio/AdventuresInOdyssey'' has many of these.
** John Avery Whittaker is veritably [[VagueAge the oldest character in the show]], and yet forms friendships with many of the other characters. The closest of these are likely his relationships with Connie Kendall and Eugene Meltsner, who began the show as both high school and college students, respectively.
*** Whit is also trusted by most, if not all, of the kids who come into Whit's End each day.
** Bernard Walton and Eugene also form a close bond, particularly after the revelation that they are distantly related. This is especially showcased in the episode "First-Hand Experience", the beginning of their [[RoadTripPlot Road Trip]] saga.
** Jason Whittaker (Whit's son) and Jack Allen (Whit's childhood friend) have a clear friendship from their first on-air meeting in Album #22. Due to their being created as two different sides of Whit's character, however, their bond is somewhat strained by their disagreements about taking action or risks (which comes to a head in the "Darkness Before Dawn" saga).
** Wooton Bassett is "a man in his thirties" who [[ManChild never grew up]]. He forms friendships with many of Odyssey's kids, particularly Grady.
* ''Radio/OurMissBrooks''
** Miss Brooks' best friend and confidante is her landlady Mrs. Margaret Davis. Mrs. Davis states a few times that she is "sweet sixty" (i.e "The Big Game"). Miss Brooks is hinted to be in her late twenties in several episodes of the program.
** Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks herself would surely object to the label!
[[/folder]]

[[folder:Theater]]
* Ruthlessly zigzagged and {{Deconstructed}} in the plays of Creator/PeterShaffer, as he [[DownerEnding never shows them to end well]]. By the end of ''{{Theatre/Equus}}'', [[MyGodWhatHaveIDone Dysart laments that he has reduced Alan]] to an EmptyShell in his attempt to cure him, in ''The Royal Hunt of the Sun'' [[OutsideGenreFoe Pizarro murders Atahualpa, destroys his civilisation and plunders its riches]] in spite of having formed a close bond with him, and [[AlwaysSomeoneBetter Salieri destroys Mozart out of sheer envy and spite for his God-given musical talents]] in ''{{Theatre/Amadeus}}''.
* In Creator/WilliamShakespeare's ''Theatre/AsYouLikeIt,'' twenty-something Orlando's elderly servant Adam helps him to run away, and the two become devoted to each other as a result.
* Arguably the most interesting part of the second half of Shakespeare apocrypha ''Edward III'' is Edward the Black Prince's relationship with Audley, an elderly and loyal knight of his entourage. The friendship's crowning moment is Edward's impassioned speeches to the wounded Audley:
-->'''Prince Edward''': Dear Audley, if my tongue ring out thy end,\\
My arms shall be thy grave! What may I do\\
To win thy life, or to revenge thy death?\\
If thou wilt drink the blood of captive kings,\\
Or that it were restorative, command\\
A Health of kings' blood, and I'll drink to thee;\\
If honor may dispense for thee with death,\\
The never dying honor of this day\\
Share wholly, Audley, to thy self, and live.
* ''Theatre/WesterosAnAmericanMusical'': The only other person Davos is seen consistently getting along with besides Stannis is Stannis' young daughter Shireen.
[[/folder]]

[[folder:Video Games]]
* ''VideoGame/PokemonRubyAndSapphire'': In both the originals and the remakes, the 10-year-old PlayerCharacter actually befriends Maxie and Archie -- the leaders of Team Magma and Team Aqua respectively -- after their HeelFaceTurn. The latter is especially buddy-buddy with the player even as the [[FriendlyEnemy antagonist]], and the former is fairly courteous as well. Even in ''VideoGame/PokemonUltraSunAndUltraMoon'' the two are fairly decent towards the 11-year-old player, [[TheBadGuyWins all things considered]].
** ''VideoGame/PokemonScarletAndViolet'': Because Naranja/Uva Academy allows people of many different ages to enroll, there's no clear ages to the main cast. However, from the three friends the protagonist makes, only Penny is around their same age, while Nemona and Arven are clearly older. Arven even reffers to the main character as his best friend. In the DLC the protagonist also befriends Kieran and Carmine. While the former is around the same age, the latter is his older sister.
* ''Franchise/TheLegendOfZelda'':
** In ''VideoGame/TheLegendOfZeldaPhantomHourglass'', while the fairy Ciela rightfully calls out 20s-30s Linebeck for being a coward, he seems to develop a real friendship with the twelve-year-old Link, even helping him save the world.
** In ''VideoGame/TheLegendOfZeldaBreathOfTheWild'', Daruk is close friends with 17-year-old Link in the backstory. In the present, Link also becomes friends with Riju, the Gerudo Chief who is [[AChildShallLeadThem a young teenager at the oldest]].
* ''VideoGame/MetalGear'':
** The strong friendship (and eventual fallout) between [[FallenHero Big Boss]] and [[BigBad Zero]], 26 years his senior, is a key plot point for the franchise as a whole.
** The ChildProdigy Sunny (eight years old) and the [[HeelFaceRevolvingDoor ever morally ambiguous]] medical worker Naomi (late thirties/early forties) form something of a friendship in ''VideoGame/MetalGearSolid4GunsOfThePatriots.''
* Creator/BioWare and this trope are good friends:
** The Player Character and Mission in ''VideoGame/KnightsOfTheOldRepublic'' (technically, Mission and ''everyone''), as well as Jolee and everyone.
** ''Franchise/MassEffect'':
*** Shepard and Tali, and Shepard and Liara. In fact, for Liara and Shepard it is both ways. Liara is 106, the asari equivalent of being barely out of her teens, and Shepard is in his/her early thirties. Anderson and Shepard also are like this, with Anderson being 46 in the first game.
*** Wrex from ''[=ME1=]'' and Samara from ''[=ME2=]'' (both roughly [[ReallySevenHundredYearsOld 1,000 years old]]) also count. The Shepard/Anderson friendship also has as Anderson acting as a [[ParentalSubstitute father figure]] to Shepard. Joker (late 20s/early 30s) and Dr Chakwas (late 50s/early 60s at the youngest) seems similar.
** ''VideoGame/DragonAgeOrigins'':
*** Alistair and Wynne have a warm, somewhat flirty relationship with May-December subtext, though remains platonic.
*** Wynne also counts with Leliana and the Warden him/herself (who is usually stated as being relatively young). Though his age is not clear, Sten and the Warden may also count.
* ''Franchise/KingdomHearts'':
** Sora's constant companions WesternAnimation/DonaldDuck and WesternAnimation/{{Goofy}} are [[VagueAge more or less]] adults, though this is a little obscured with them being anthropomorphic animals. Although his strongest feelings are for Riku and Kairi, who are his age.
** The games also have a similiar friendship between Riku and Mickey.
** Axel's friendship with Roxas, as Axel is an adult and Roxas is in his early teens. His relationship with Roxas and Xion is very like this in ''358/2 Days'', with the two both looking at Axel kinda like a big brother for his knowledge on the opposite sex, emotions, relationships... he in turn is very protective of them, and his anger at being forgotten makes a lot more sense considering this.
** And again with [[VideoGame/KingdomHeartsBirthBySleep Aqua, Ventus and Terra]], which is all the more symbolic, considering the ThemeNaming going on, and the fact that [[spoiler: Ven' heart is sleeping inside Sora, and Terra and Aqua are the ones who chose Riku and Kairi to be the next Keyblade wielders (accidentally so in Aqua and Kairi's case).]]
* ''VideoGame/TalesOfSymphonia'': 17-year-old Lloyd's best friend is 12-year-old Genis. During the game he also makes friends with Zelos (21) and Regal (32). And to ''really'' screw with your head, [[spoiler: Presea is biologically and mentally twelve, but chronologically ''twenty-eight''.]]
* In ''VideoGame/TalesOfTheAbyss'', this is pretty much true for Jade (mid-thirties) and the entire rest of the party, who are in their teens (except for Guy, who's in his early twenties). It's the most pronounced with Anise, who is thirteen and is frequently paired up with him when [[LetsSplitUpGang the party splits up]] in cutscenes and plot events.
* ''VideoGame/TalesOfVesperia'' (noticing a theme here?) does this too; Karol (12) strikes up a good friendship with most of the party, but in particular his guild subordinate (and main protagonist) Yuri (21), who calls Karol 'Boss'. With one exception, none of the playable cast is over 21; that exception being Raven, who at 35 gets the somewhat sarcastic nickname "Old Man".
* ''VideoGame/TalesOfXillia'' has the largest age gap so far if we're going by human years with the Elize as the youngest at 12 and Rowen as the oldest at 63. The age gap is large enough that he's old enough to be a grandfather to three of the party members and father to the other two since the next oldest is Alvin at 30.
* Several examples are possible in the ''Franchise/FireEmblem'' series, thanks to the [[RelationshipValues support system]].
** ''VideoGame/FireEmblemTheSacredStones'' has, among the more notable ones, Amelia (~15) and Duessel (old enough to be her grandfather, likely in his mid 50's), who even get a double-ending where Amelia becomes Duessel's [[TheLancer "most trusted companion"]]. [[spoiler:The fact that Duessel reunites Amelia with her MissingMom Melina, whom he rescued from the bandits who kidnapped her when Amelia was a child, probably helps a lot.]] Duessel also has good relationships with Ephraim (around early 20's), Cormag and Knoll (both in their mid 20's). Ewan (13-14) and his magic teacher Saleh (age not stated, but most likely in his mid to late 20's) also get a double-ending. There's also Gilliam (likely around his late 30's) and both Franz and Neimi (around Amelia's age, if not slightly older, who ''also'' has one with Garcia).
** ''[[VideoGame/FireEmblemTheBlazingBlade Blazing Blade]]'' has Serra (a 16 year-old cleric) and Oswin (a knight in his mid 30's), albeit [[MayDecemberRomance they can also become a couple]]. Canas (probably in his late 20's or early thirties) also develops one with Nino, who is 14.
** In ''VideoGame/FireEmblemAwakening'', there's Gregor (a mercenary in his 40's/maybe even 50's) and either Lon'qu (early-to-mid 20's MasterSwordsman) or Ricken (a pre-teen/early teenage [[ChildProdigy mage]]).
** In ''VideoGame/FireEmblemFates'', Yukimura (a BadassBookworm implied to be in his early 40's) has this with Sakura (a WhiteMagicianGirl in her early-to-mid teens ''tops''). In one of the DLC stages [[SweetTooth she tells him that she misses Hoshidan dango]], so [[MundaneUtility he outfits one of his Automatons to make her some]].
** Garreg Mach Monastery in ''VideoGame/FireEmblemThreeHouses'' generally houses students from ages 15 to 18 in the same class, but there are a few students who are much older, with the most stand-out example being Balthus (''26'') having a support with Lysithea (15), despite being over ten years her senior. Hanneman, a teacher at 51 years old, also has this dynamic with every student and even some teachers, including the protagonist.
*** Another example from the same game is Annette and Mercedes, who are 16 and 22 respectively at the beginning of the game. They're best friends and are established to have known each other for a couple years prior to enrolling at the Officer's Academy.
* ''VideoGame/PrincessMaker2''
** The main character's daughter can have these dynamics with... a centuries-old dragon who lives in the desert. The dragon is an old friend of the girl's father figure, back when he was a wandering warrior, and being a ChivalrousPervert as well he endlessly teases the girl about her figure (and can give her the Dragon Tights, one of the outfits required for the dancing competition in the Harvest Festival).
** Additionally, the dragon has a young and reckless grandson. If the heroine beats said grandson in battle when she's older than 15, [[LoveAtFirstPunch the young dragon falls in love with her]] and the old one can give the main character the chance to have their kids engaged. It's interesting to point that said dragon is ''one year younger'' than the main character.
* ''VideoGame/{{Mother}}'':
** In ''VideoGame/EarthBoundBeginnings'', the kids (well, [[GuestStarPartyMember the first two]], anyway) befriend Teddy, a grown-up gangster from [[NoCommunitiesWereHarmed Ellay]].
** In ''VideoGame/Mother3'', almost all of the 13-year-old Lucas' party members are older than him, save [[TeamPet Boney]]. Kumatora's [[VagueAge age is vague]], but she seems to be in either her early or late teens. Duster's age is also vague, but he seems to be in his late twenties to early 30s. All three of them [[TrueCompanions depend on and trust each other]].
* Chopin and Polka in ''VideoGame/EternalSonata''. They're so close that fans try to [[FanPreferredCouple pair them together]] even though Polka's twenty-five years younger than him (and officially paired with Allegretto).
* ''VideoGame/NamcoXCapcom'':
** Felicia and Klonoa are made of this. She is a Catwoman who's somewhere in her late teens or early 20s, while he is a Kaze no Neko ("Cat of the Wind") in his early to mid teens. Both of them are cheerful, positive and playful people who decided to be friends and stick together just because ''both of them are cat people with long hair''.
** Much for King's wall-banging despair, they try to make him join their group, no matter how many times he tries to explain them that he's just a short-haired human Luchador wearing a jaguar mask.
* VideoGame/ProfessorLayton, especially in ''VideoGame/ProfessorLaytonAndTheUnwoundFuture'', features Layton (34/35 in the prequels, 37 in the sequel/main trilogy) and Luke's (10 in the prequels, 13 in the sequels/main series) friendship. ''Unwound Future'' features a statue of a man with a top hat resembling Layton, and a young boy who looks like Luke, and the story on it describes a similar friendship between an author and a sick young boy until the boy died of his illness.
* ''VideoGame/SengokuBasara'' has several examples. There's Masamune (19) and Kojuro (30ish), who are sometimes joined by Itsuki (12); Yukimura (17) and Sasuke (mid 20s); Ieyasu (15) and Motochika (20s); Yoshihiro (60s/70s) and Keiji (22); and Mitsunari (19ish) and Yoshitsugu ([[VagueAge prob 30s]]).
* ''Franchise/TouhouProject'':
** [[RealityWarper Yukari]] and [[CloudCuckooLander Yuyuko]], the former several millenia-old at the very least and the latter (originally) an ordinary human. Even after Yuyuko has spent about a thousand years as a CuteGhostGirl Yukari is still many times her age and outclasses her in every way possible, but they remain close friends.
** Yukari also has a VitriolicBestBuds-style relationship with Reimu, who still is human and whose age is a double-digit number. Frankly, most youkai with human friends are like this.
* [[CoolOldGuy Kraden]] is friends with all of the player characters (most of whom are {{Kid Hero}}es) in the ''VideoGame/GoldenSun'' games. Piers may or may not be ReallySevenHundredYearsOld, so his friendship with Felix's group likewise fits the mold-- in fact, he says that he'd [[VagueAge rather not admit his age]] so it doesn't affect how they see him. [[NeverMessWithGranny Obaba]] becomes friends with the heroes of ''The Lost Age'' and ''Dark Dawn'', as does her baby great-grandson Eoleo (on the [[GooGooGodlike younger end]] of the relationship in ''TLA'', and the [[FutureBadass older end]] of the one in ''Dark Dawn'').
* ''VideoGame/Persona3'' is full of these with both the male and female protagonists. This is the case for Tanaka, the Devil Social Link, the elderly couple (Mitsuko and Bunkichi), who have the Hierophant Social Link, and Mutatsu the monk, who serves as the Tower Social Link, but also with Maiko, the Hanged Man Social Link, who is an elementary school student in comparison to the protagonist (a junior in high school), and your mutual friend Sun Social Link Akinari Kamiki, a writer in his twenties. In addition, party members 10 year old Ken Amada and 18 year old Akihiko Sanada become good friends over a mutual love of beating things up.
* ''VideoGame/Persona4'':
** Alongside the main character's younger cousin Nanako befriending the rest of the party, we have the MC and the persons holding the Death (a widow in her 60's), Temperance (a stepmother in her early/mid 30's) and Devil (a HospitalHottie in her late 20's) Arcana Social Links.
** Yukiko became close to Kanji's mother for work, which is why she has embarrassing knowledge of Kanji's formative years (as shown in ''Arena'') and asks him whether he's hiding his bad grades from the latter.
** The UpdatedRerelease ''Persona 4 Golden'' adds Adachi, a bumbling twenty-three year old police officer, as a Social Link of the newly-introduced Jester[[spoiler:/Hunger]] Arcana.
* ''VideoGame/{{Ib}}'' has the titular Ib, a nine year old girl, and Garry, who seems to be a young adult. The two become good friends due to having to work together to survive a really strange art gallery.
* In ''VideoGame/TheKingOfFighters'' there are several examples:
** The Japan team is formed by Kyo (20), Benimaru (21)... and Daimon (29). The latter started as more or less the mediator between [[VitriolicBestBuds the two others]], then they became TrueCompanions.
** Also K' (age unspecified, but seems to be 18 ''tops'') and Maxima (29). As well as Kula (14) and Chin (mid ''80's''); this one was lampshaded when Kensou (who's 19 by the way) mistakes them as having a MayDecemberRomance.
** This trope becomes a huge plot point in the Tales Of Ash saga. [[spoiler: 16/17 years old Ash Crimson had this with 27-year-old Elisabeth Blanctorche, who doubled as his OnlyFriend. So to protect the only person he truly loved and cared about, Ash staged a massive BatmanGambit that involved attacking and depowering both Chizuru and Iori, making himself the most hated fighter all around and go against everyone and everything he knew... to keep Elisabeth safe and make sure she won't have to fulfill her destiny to fight the current Nebulous Organization, Those of the Past. So yeah, for his much older friend, Ash ''staged the whole last arc and ended up {{ret gone}}d''.]] It's lampshaded by Kim in ''XIII'', even: [[spoiler: if Kim fights Ash he will refer to Elisabeth as Ash's [[ParentalSubstitute "guardian"]] and ask him to return to her side, threatening to drag him back by force if needed; Ash will not just refuse to leave, but he will correct Kim on how "Betty" isn't his caretaker.]]
** Also the Ikari Warriors Ralf (39) and Clark (34) are much older than their fellow fighters/mercenaries Leona (19) and Whip (16-17 apparently), but the four have extremely strong bonds and both Ralf and Clark treat the orphaned Leona [[BigBrotherMentor like a younger sister]] (in addition to her being the adoptive daughter of Heidern, their boss.)
** The Psycho Soldiers team is formed by Athena and Kensou (both around 18 years old) and their master Chin (an old man). Later on they are joined by Bao, who is 12.
* In ''VideoGame/{{Borderlands 2}}'', Tiny Tina, a [[HarmfulToMinors troubled]] and [[CuteAndPsycho demented]] thirteen-year-old DemolitionsExpert, has this with [[TheHero Roland]] (somewhere in his 30s), [[BruiserWithASoftCenter Brick]] (around the same), and [[TestosteronePoisoning Mr. Torgue]] (in his 40s). Roland serves as a ParentalSubstitute, while Brick and Mr. Torgue are enablers of her love of explosives and bringing destruction upon the bandits of the waste. In the ''Tiny Tina's Assault on Dragon Keep'' DLC, Lilith plays the role of a CoolBigSis to Tina while Mordecai simply just puts up with her (though they bond over the fact that they both love [[Series/DowntonAbbey the same show]]).
* The ''Franchise/SonicTheHedgehog'' games have a few examples:
** Downplayed with Amy and Cream, as they are both children, but still present as Amy is twice Cream's age (Amy is twelve, and Cream is only six).
** Sonic and Knuckles are also this for Tails. Him being 8 and Sonic and Knuckles being 15 and 16 respectively, according to the manual of ''VideoGame/SonicHeroes''.
** In ''VideoGame/SonicRush'', the 14-year-old Blaze eventually befriends Cream as well. [[VideoGame/SonicRushAdventure The sequel]] also introduces Marine, who's seven.
** Team Chaotix consists of the 20-year-old Vector the Crocodile, the 16-year-old Espio the Chameleon, and the 6-year-old Charmy Bee.
** Most of them are like this with the [[Franchise/SuperMarioBros Mario cast]] in the ''Mario and Sonic'' series. Mario is in his mid 20s (and ''Yoshi's Island DS'' shows most of the cast were babies at the same time) while most of the Sonic gang is in their teenage years, but the cast sees each other as friendly rivals. Perhaps the only exceptions are Bowser and Dr. Eggman.
* Swaine to Oliver and Esther in ''VideoGame/NiNoKuni.'' Oliver is about twelve and Esther is about fourteen. Swaine is about twenty-five to thirty ([[spoiler: judging from the fact that when the party meets his younger self fifteen years in the past, he looks slightly younger than Oliver]]), but ''looks'' [[YoungerThanTheyLook even older]] due to his extremely unkempt appearance.
* Clementine from ''VideoGame/TheWalkingDeadTelltale'' mostly has parental figures in the first season, most notably Lee (with the possible exception of Ben, who's about six years older than her) but in the second game her relationship with Luke and Nick takes place on far more equal terms. She actually spends a lot of time ''parenting'' Nick, who's likely well into his twenties. In season three, with Clem now 13, she develops a close friendship with the PlayerCharacter Javier García, who is in his early to mid 30s. In season four, 16-year old Clem gets to be the older part of such dynamic for the first time, due to her close bond with [=AJ=], who's 5.
* ''VideoGame/TomodachiLife'' doesn't really have an age distinction beyond "adult" and "kid". That being said, an Adult Mii and a Kid Mii can develop a friendship, or even become best friends.
* Possible (like over half tropes) in the ''Sims'' series games. In ''VideoGame/TheSims2'' only the family you're playing ages, and thus a friendship between two people of the same age can become intergenerational and viceversa so maybe not really this trope. ''VideoGame/TheSims3'' premade examples of this include River [=McIrish=] (teen with 5 - out of 14 - days to young adult) and Claire Ursine (adult\middle aged with 16 - out of 21 - days to Elder), and (Ambitions expansion pack) Jade Greenwood (teen with 14 days to young adult) and Silver Racket (adult with 13 days to elder).
* In most ''VideoGame/HarvestMoon'' games, you are a 20-something year old who can befriend people of various age groups.
* ''VideoGame/XenobladeChronicles'':
** ''VideoGame/XenobladeChronicles1'': Riki is a 40 year-old [[RidiculouslyCuteCritter Nopon]] with eleven children who becomes friends with everybody with the party whose ages range from 18 to 27, and was already previously acquainted with Melia. PlayedWith with Melia herself as while at 88 years old, she is by far the oldest member of the group, she is a [[HalfHumanHybrid Half High-Entia]] meaning she ages and matures more slowly and as such, has the same level of maturity and experience as her younger companions.
** ''VideoGame/XenobladeChronicles2'': [[OlderThanTheyLook 15 year-old salvager Rex]] is shown to have long been friends with Azurda, affectionately known as "Gramps", who, as a Titan, has been alive for several centuries. He also later becomes friends with Mòrag, Zeke and Nia; the former two of whom are at least ten years older while Nia is [[spoiler:possibly centuries older as a result of being a Flesh Eater Blade.]]
** ''VideoGame/XenobladeChronicles3'': As Kevesi and Agnians in the world of Aionios do not live younger than ten years, the Nopon companions Riku and Manana are automatically this to the Ouroboros group despite their unknown ages. [[spoiler: And given Riku's MysteriousPast, he is possibly [[ReallySevenHundredYearsOld centuries old]] or ''older than Aionios itself.'']]
** ''VideoGame/XenobladeChroniclesX'': Lin (13) with most other characters by virtue of being the youngest human not in stasis by several years. Most notably with Elma (29) [[spoiler:true age unknown but likely much more than that as it is stated that 29 years ago was when she [[AlienAmongUs first came to Earth]] rather than when she was born]].
* In ''VideoGame/TheLastOfUs'', Joel is a grizzled survivor in his 50s who befriends the 14-year old Ellie over the course of the game. There's also Joel and Henry, who's 25.
* ''VideoGame/TheLastOfUsPartII'': Ellie, now 19, befriended Joel's brother Tommie and his wife Maria, both about Joel's age. Her girlfriend, Dina (also about 19), seems to be friends with a [[FriendToAllChildren majority of kids who live in Jackson]]. Dina herself used to be friends with a man named Eugene (he's a PosthumousCharacter, but he was probably about 50-60). [[spoiler:There's also Abby (likely early twenties), who befriends Lev (13)]].
* ''VideoGame/{{Overwatch}}'' has the grubby Aussie criminals Junkrat at 25 and Roadhog at 48.
* [[Anime/MashinHeroWataruSeries Wataru]] ends up striking a meaningful friendship with [[Anime/CrossAnge Ange]] in ''VideoGame/SuperRobotWarsX''. He even becomes Ange's MoralityPet. Ange says more than once that she just can't say no to him. Moments just after he shows up [[Anime/CodeGeass Lelouch]] practically becomes the CoolBigBro and BigBrotherMentor that Ange needs and deserves to have. Ange's interactions with both Wataru and Lelouch play a role in making her character more benevolent and reasonable. [[spoiler:So much that when she finds Sylvia walking on her own, she offers her a hand to restore order to Misurugi and establish Cafe Ange in her old home]].
* In ''VideoGame/BattleFantasia'', Marco (age 9) and Cedric (age 16) end up becoming friends. Granted, this is mostly one-sided on Marco's side and Cedric mostly finds him annoying and is following him around because he can't, in good conscience, leave a kid alone. However, by the end of Cedric's story mode, he acknowledges he ended up considering Marco a friend and even [[spoiler: decides to become his Magic teacher]].
* ''VideoGame/RedDeadRedemption2'': Most of the Dutch Van Der Linde gang members are friends, spanning from middle-aged men like [[TheLeader Dutch]] and [[NumberTwo Hosea]] to even children like Jack Marston.
** "The Veteran" Stranger mission involves the 36-year-old Arthur Morgan befriending an elderly Civil War veteran named Hamish, who (despite having a prosthetic leg) never lets anything bad get him down. The two bond over chatting, finding Hamish's horse Buell, fishing for muskies, and hunting wolves. Sadly, things come to an end when Hamish gets gored to death by a massive wild boar, but Arthur shoots the boar in the end, remarking "We got him, old man."
** Relating to "The Veteran", the same thing can happen with John Marston if he finishes "The Veteran" for Arthur (or if Arthur never met Hamish at all).
* Ivor and Jesse in ''VideoGame/MinecraftStoryMode''. Though Ivor (previously a member of the legendary Order of the Stone) began the series as the antagonist, he has a [[HeelFaceTurn Heel-Face Turn]] and helps Jesse defeat the Wither Storm. By Episode 5, he is a prominent member of the group, and his friendship with Jesse develops over the remainder of the season. [[spoiler: When he returns as a ninja in Season 2, you have the option to hug him.]]
* ''VideoGame/RoadToGuangdong'' revolves around the relationship of the player character, a young girl in her early-20s, with her grand-aunt, who she barely knew until she needed to chauffeur her to a cross-country funeral.
* In ''VideoGame/WorldNeverland,'' it's possible for a child character and an adult character to become friends. However, they can't max out their friendship and become Best Friends, as the adult will tell the child to wait until they're older. If the child character grows up and then becomes Best Friends with their adult friend, they'll even have special dialogue acknowledging how glad they are that they can finally be good friends with their adult friend.
* PlayerCharacter V (27), from ''VideoGame/Cyberpunk2077'' gets to befriend quite a lot of older characters, due to this being a universe with advanced rejuvenation treatments and aesthetic implants. Most notably, the fixer [[CoolOldLady Rogue]] and TheRockstar Kerry Eurodyne, both about 70-80. They also start off as friends with their ripperdoc, Viktor, who is about 60. There's also [[CorporateSamurai Takemura]], who looks to be about 50-60, and might possibly be older.
* ''{{VideoGame/Yakuza 3}}'' has a quite sweet example between 8-year-old orphan Izumi and twenty-something yakuza lieutenant Mikio. The two meet when Mikio's yakuza family try to shut down the orphanage Izumi lives in, and bond over a mutual love of dogs, eventually taking in and caring for a stray puppy together.
* ''VideoGame/{{Skullgirls}}'':
** Played with when Annie and Beowulf become friends at the end of their story arcs, but the intergeneration aspect is the reverse of what it looks like. The public sees Annie, a 15-ish actress, befriending Beowulf, a 37-year-old pro wrestler, but Beowulf is a mortal man, and Annie is [[ReallySevenHundredYearsOld very, very much the elder of the two]].
** At the end of her story mode, Umbrella (age 11) has become good friends with Filia and Painwheel (both around 16).
* ''VideoGame/MyTimeAtPortia'' has the elderly scholar Isaac and Polly, a studious young girl and the middle child of three sisters, who are best friends due to their common interest in historic literature and the game Cross Five.
* ''VideoGame/MrSaitou'': Brandon, a curious and outgoing child, and Mr. Saitou, a weary middle aged salaryman, become good friends over the course of their adventure in the dream world. [[spoiler: The ending scene implies it may not have been a dream and they became good friends in real life.]]
* ''VideoGame/FinalFantasyIX'': Steiner (33 years old) doesn't have very good relationships with most of the cast, due to his uptight LawfulStupid attitude. One of the few exceptions is Vivi (physically 9 years old, [[ArtificialHuman chronologically 6 months old]]), whom Steiner deeply respects.
* ''VideoGame/FinalFantasyXII'' has a VillainousFriendship example between [[MadScientist Dr. Cid]], who's 58, and [[TheConqueror Vayne]], who's 27.
[[/folder]]

[[folder:Visual Novels]]
* ''Franchise/AceAttorney'' has quite a few examples.
** The biggest being Kay Faraday (17) and Dick Gumshoe (32), who end up acting like children when the other is around (they first met at 10 and 25, respectively). To an extent, Edgeworth (26) and Kay, Phoenix and Maya (24 and 17 when introduced), Nick and Pearl (8/9) and Gumshoe and Maggey (22/23) all count as well.
** Machi and Lamiroir in ''VisualNovel/ApolloJusticeAceAttorney'', although that one's more like a case of ParentalSubstitute.
** The Judge seems to develop, over time, an odd friendship with much of the main cast (especially Phoenix, as seen in ''Apollo Justice''.) That doesn't stop him from giving you penalties, though - work is work.
** ''Dual Destinies'' shows that [[spoiler: 21-year-old Simon Blackquill and 11-year-old Athena Cykes]] used to have this years ago, before things went FromBadToWorse for them. [[spoiler:Though they might have retaken it in the Good Ending, where 28-year-old Simon is saved from being unfairly executed much to 18-year-old Athena's joy.]]
* [[TheHero Shirou]] and [[TokenMiniMoe Ilya]] in ''VisualNovel/FateStayNight''. [[spoiler:In appearance. In reality, the age difference is less than five years, with ''Ilya'' being the older one. There are some [[BigBrotherAttraction pretty]] [[ParentalAbandonment twisted]] [[CloneDegeneration reasons]] why this whole situation came about.]] Their relationship is very much that of the brother and sister kind; [[spoiler:ironically, Shirou's adopted father Emiya Kiritsugu is Ilya's biological father, making them actual siblings by adoption. Ilya appears to be aware of this from the start, Shirou only learns of it in one route.]]
* ''VisualNovel/{{Narcissu}} ~ Side 2nd'': Setsumi (15) and Himeko (23). The trope is invoked in this case, as Himeko was trying to finish the list of the 10 things that she wanted to do before her illness killed her, with one of the items being that she wanted to become friends with somebody significantly younger than herself. [[spoiler: This trope applies even more with regards to Himeko and "Nello" in flashbacks, although the other girl's exact age is never given.]]
* ''VisualNovel/SpiritHunterNG'':
** Ami is good friends with Yuri and Kaoru, despite her being elementary-aged and them being high-schoolers. This is explained as Ami and Yuri living in the same apartment building, with Yuri playing with Ami when Ami's mother was too busy with work to look after her.
** While Akira's first two companions are both around his age, the second set are Ban and Rosé, a middle-aged man and a woman who keeps her age a secret, but frequently teases Akira for being young and 'cute'. Having adults who're experienced with supernatural affairs proves very useful to Akira, though that doesn't stop him from bickering with them like he does with his high-school friends.
[[/folder]]

[[folder:Webcomics]]
* In ''Webcomic/AkiChansLife'' (which is the sequel to the above mentioned fan fiction ''Fanfic/TheSecondTry'') the titular Aki Ikari and former pilot [[Anime/NeonGenesisEvangelion Rei Ayanami]] are best friends, despite (or perhaps, because of) the big and weird differences in age between the two.
* In ''Webcomic/AlfdisAndGunnora'' Alfdis and her teacher Lord Frey appear to have as much a friendship as a Mentor/Student relationship.
* ''WebComic/BatmanWayneFamilyAdventures'': Due to the sheer weirdness of the Wayne family (being superheroes and all), a lot of the Bat kids have friends/[[HonoraryUncle honorary family members]] who are several years older than they are. One example would be Harley Quinn and Poison Ivy. Both women are well into their thirties (Ivy was an effective villain back when Dick was still Robin), yet the episode "Branching Out" shows them becoming friends with Spoiler and Orphan (both of whom are in their teens).
* ''Webcomic/CirqueRoyale'': Seven-year-old Red is close friends (and being mentored in strongmen acts) by Ron, who is elderly.
* Julian Sands (adult camel) and Jarrad Dryandra (numbat child) in ''Doc Rat''. Their friendship [[PaedoHunt comes under scrutiny]] when [[spoiler:Julian comes out of the closet]].
* Pandora (old even for an immortal) and Sarah (18) from ''Webcomic/ElGoonishShive''. To a lesser extent, Mr. Tensaided (somewhere in his thirties or forties) and Sarah, courtesy of [[TabletopGame/MagicTheGathering Magickal]] [[BlandNameProduct Gatherings]].
* In ''Webcomic/GirlGenius'', Agatha Heterodyne and the Jaegermonsters who follow her. [[spoiler: And [[EpilepticTrees possibly]] just about everybody with Airman Third Class Axel Higgs "the Unstoppable".]]
* Bob (probably in his twenties) and the elderly Mrs. Primrose in ''Webcomic/TheInexplicableAdventuresOfBob.''
* Richard and Cale from ''Webcomic/LookingForGroup''. Richard is apparently hundreds of years old.
* Alcolla (preteen) and Yakuv (unspecified, but at least mid-30s) in ''Webcomic/{{Reliquary}}''.
* ''Webcomic/TheShufflers'': Märchen is in his 30s at least while Hiddenite is a young man. Hiddenite starts off being a bodyguard to Märchen, but eventually the two come to care about each other as friends.
* In ''Webcomic/LottaSvardWomenOfWar'', Taimi begins working at the Evacuation Center for the Fallen (where she cleans up corpses of dead soldiers for presentation before their burial) with an elderly man named Mr. Ritola, otherwise known as "The King of the Dead". The two of them admit to seeing each other as surrogate grandfather/granddaughter, and remain in touch via letters once the center closes down.
* Riff and Dr. Schlock from ''Webcomic/SluggyFreelance'' (in their late 20's and late 80's, respectively) bond over their shared love of [[MadScientist Mad Science]].
* Many relationships in ''Webcomic/TowerOfGod'', due to the different life spans of the races and the life-prolonging characteristics of Shinsu.
** Kids like Khun and Hatz are in their late teens while their good friend Shibisu is in his 30s, whereas Bam is probably several hundred years old.
** Anaak has an OddFriendship going on with her [[NotBloodSiblings aunt Endorsi]], who is actually much younger than her.
* Jinx of ''Webcomic/TheWhiteboard'', about ten years old, is on friendly terms with pretty much the whole adult cast, and seems especially fond of Doc. (Note: the artwork can create an apparent resemblance, but Jinx, an Arctic fox, is not related to either Doc or Cara, both of whom are polar bears.)
* ''Webcomic/WildeLife'': Oscar becomes 16-year-old Cliff's friend and SecretKeeper after Cliff passes out on his porch [[OurWerewolvesAreDifferent in wolf form]]. Cliff's parents are realistically concerned that he's spending so much time with a strange adult from out of town but appreciate the positive influence on Cliff's behaviour.
-->'''Oscar:''' I'm [[https://www.wildelifecomic.com/comic/452 twenty-five.]]\\
'''Kevin:''' Isn't that too old to be friends with my brother?\\
'''Oscar:''' You know, I thought the same thing, but he wouldn't leave me alone.
[[/folder]]

[[folder:Web Original]]
* In the ''Raising Corpse'' [[https://youtu.be/Vb6vCnLlAvs skits]] (which feature a fictional and humorous version of the life of a young Creator/CorpseHusband), 7 year old Corpse has a surprisingly wholesome and heartwarming friendship with his babysitter's [[TheDitz ditzy]] {{Fratbro}} boyfriend Kyler.
* In ''Literature/{{Twig}}'', Gordon, a thirteen-year-old HumanWeapon, is good friends with a pair of older experiments called Dog and Catcher, and he even offers Dog a great deal of comfort just by being near him.
[[/folder]]

[[folder:Western Animation]]
* ''WesternAnimation/ThreeTwoOnePenguins'': Jason and Michelle, two seven-year-old kids, are friends with Zidgel, Midgel, Fidgel, and Kevin, who all look like they are in their thirties.
* ''WesternAnimation/AdventureTime'':
** In the pilot, [[Characters/AdventureTimeFinn Finn]] is twelve and [[NonHumanSidekick Jake]] is twenty-eight, while in the series Finn is 13 and WordOfGod specifying Jake is twenty-eight in "magical dog years" -- which could possibly make him younger than Finn in absolute terms but he's certainly of adult age for his species. They're also adoptive brothers, Finn having been raised by Jake's parents.
** Technically [[KidHero Finn]] [[OddFriendship and]] [[OurVampiresAreDifferent Marceline]], since she's [[ReallySevenHundredYearsOld Really One Thousand Years Old]] (though she looks more like a teenager or young adult).
** By the same token, Finn's and Jake's friendship with [[Characters/AdventureTimePrincessBubblegum Princess Bubblegum]], who is almost as old as Marceline.
** Most recently, Marceline and the Ice King, though comparatively closer in age to each other than to the rest of the cast. [[spoiler:It used to be intergenerational, though, when she was a 7 year old child, while Simon was 40 years older.]]
** Cinnamon Bun (described by PB as "basically 30" in "Another Five More Short Graybles") and Flame Princess (14 at the start of her introduction) strike up a friendship in "Earth & Water". He ends up becoming her loyal champion.

* ''WesternAnimation/{{Amphibia}}'': Combined with InterspeciesFriendship. At least 4 characters have formed this with at least one or more person older than they are.
** Anne Boonchuy is a 13 year old girl, while One-Eyed Wally is either in his 20's, 30's, or 40's. While they got off to a bad start in the first episode with interactions between them being anything but friendly afterwards. They began to warm up to each other after the events of "Toad Tax", and they officially became friends as of "Wally and Anne". Which continued on to episodes such as "Swamp and Sensitivity".
** Sasha Waybright is a 13 year old girl, while Captain Grime is somewhere in his 50's or 60's. While they got off to a bad start immediately after Sasha arrived in Amphibia, with Grime imprisoning Sasha for about a month, and Sasha manipulating his guards into quitting their jobs, much to Grime's irritation. But they began to see each other as equals after the events of "Prison Break", with Grime even making Sasha his lieutenant. He even gives Anne an angry glare after he saves an injured Sasha from falling to her death in "Reunion". Ever since then, Sasha and Grime became as thick as thieves, and fought by each other's side during their banishment, even after they discovered King Andrias's true colors and formed the resistance along with the citizens of Wartwood. Grime's friendship is what inspired his HeelFaceTurn in the entire show, and sacrificed his left arm to save Sasha from a fatal blow in "All In". When it came time to say their goodbyes, the two go into OcularGushers and tell each other that they'll miss each other very much.
** 13 year old Marcy Wu quickly formed this with the over 1000 year old colossal 30ft tall King Andrias Leviathan. Within their first few minutes of meeting each other, Marcy quickly appeals herself to Andrias by ignoring social protocol, climbs into the pocket of his robe, and then gives him a roblox pin as a friendly gift of friendship. While Andrias tries to downplay their connection, Marcy's energy and kindness towards him was enough for him to go out of his way to convince the Core not to kill her. Even after betraying, stabbing, and letting his master possess Marcy. Andrias still cared about Marcy very much as Andrias expresses guilt whenever interacting with the Core possessed Marcy (aka Darcy) and has a massive MyGodWhatHaveIDone breakdown after listening to a letter from his former frog friend Leif. After this, Andrias finally has a HeelFaceTurn, and let's Anne defeat him to stop him from doing anymore damage. Immediately after his defeat, he begs Anne to save Marcy. Not caring about his own injuries. Later, Andrias finally stands up to his Master by commanding his leftover Frobots in assisting Marcy and her friends by helping them keep the Core from crashing the Moon into Amphibia. In a deleted scene, Marcy smiles back down at him, proud of him for finally doing the right thing. When the time came for Marcy to leave Amphibia for good, Marcy gave a brief but meaningful goodbye to the former king and Andrias tells her to take care of herself. Showing that despite everything that happened between them, the two still care about each other.
** During the events of "Fixing Frobo" 5 year old Polly Plantar forms a short but meaningful bond with two college students 'Ally and Jess'. While the two girlfriends did not know that Polly is a talking tadpole from another world until "Escape to Amphibia", they were very open-minded to her somewhat strange appearance and went as far as to go to the Boonchuy's home to check on her. Polly even calls them for help when she and her family were building a Christmas float for Anne's parents in "Froggy Little Christmas". Polly even embraces them after they helped save her and her family from Mr X. While they would never see each other again, Ally and Jess's knowledge on robotics helped Polly build a new body for Frobo and later became a mechanic by the 9 month timeskip in Amphibia.
* ''WesternAnimation/AtomicPuppet'': Joey is a 12-year-old kid and AP is an adult superhero (who is at least 40 years old based on some lines) turned into a talking sock puppet.
* ''WesternAnimation/AvatarTheLastAirbender'' features three cases:
** A strange friendship forms between [[Characters/AvatarTheLastAirbenderTophBeifong Toph Beifong]] (12 years old) and [[Characters/AvatarTheLastAirbenderGeneralIroh Iroh]] (64 years old) before they realize they're both on opposite sides; Toph, who has joined the Gaang since they last saw Iroh, encounters him while having a brief falling-out with the others. And when they ''do'' realize they're on opposite sides, [[spoiler: they don't care]].
** [[Characters/AvatarTheLastAirbenderAvatarAang Aang]] and Bumi (a 12 year old boy and a man well over 100 respectively), though in this case they became friends while they were both kids (HumanPopsicle complicates many things, except maybe friendship).
** One in its sequel ''WesternAnimation/TheLegendOfKorra'' between [[Characters/TheLegendOfKorraAvatarKorra Korra]], the new Avatar, and Tenzin, the previous Avatar's youngest son. It's also kind of funny when Tenzin develops a PapaWolf personality towards Korra. Korra is also a CoolBigSis to his kids.
** This is implied to happen a ''lot'' with Avatars, especially when said Avatars die young (young for an Avatar being the average lifespan of a human) and their friends and family outlive them long enough to meet their reincarnations. Korra has a close relationship with Aang's widow Katara, who served as her waterbending instructor, and quickly befriended his other teachers, Zuko and Toph, after she met them.
-->'''Avatar Roku''': Some friendships are so strong, they can even transcend lifetimes.
** Speaking of Roku, what prompted him to say this was Aang's realization that the elderly Monk Gyatso who befriended him as a child was also friends with Roku when he was young.
** Korra has a good relationship with Toph's daughters, Lin and Suyin. Lin is in her fifties and two of Suyin's children are older than Korra herself.
** This also applies to Avatar Kyoshi in ''Literature/TheRiseOfKyoshi''. Her immediate predecessor died at only 33 so his friends all go looking for his successor. She quickly bonds with his Airbender friend Kelsang, who all-but adopts her as his daughter.
* ''WesternAnimation/BatmanBeyond'': [[Characters/DCAUTerryMcGinnis Terry McGinnis]] and [[Characters/DCAUBatman Bruce Wayne]].
* ''WesternAnimation/{{Beetlejuice}}'' features this kind of friendship between Lydia, a 12 year old girl, and the titular character, a several hundred year old {{Manchild}} (who was probably in his late 30s at his time of death).
** To make things {{Squick}}y, however, it is implied that Beetlejuice does have a crush on Lydia (including having a part of his mind being an actual ''shrine'' to her). And, yes, the pairing is canon.
* ''WesternAnimation/BigCityGreens'' has Cricket Green (a country boy of about 7-9 years old) and Gloria (a barista in her early twenties).
* ''WesternAnimation/BobbysWorld'': Bobby and his Uncle Ted.
* ''WesternAnimation/TheBoondocks'' is rife with these:
** Huey and Tom [=DuBois=]
** Riley and Gangstalicious / Thugnificent
** Riley and Ed Wuncler III / Gin Rummy
** Tom [=DuBois=] and Robert Freeman / Uncle Ruckus
* ''WesternAnimation/BuzzLightyearOfStarCommand'' has an intergenerational friendship between the adult Space Ranger Booster and a little alien girl named Becky, who affectionately refers to Booster as "Pickles".
* ''WesternAnimation/ChicagoPartyAunt'' had Diane and her nephew Daniel, after the latter moved to the former's apartment while taking a gap year from college.
-->'''Daniel:''' You're not just my aunt, you're also, sadly, my best friend.\\
'''Diane:''' ''(to Bonnie)'' Did you hear that? Best friend!\\
'''[[DeadpanSnarker Bonnie]]:''' He ''did'' say "sadly".
* ''WesternAnimation/ChipAndDaleRescueRangers'': Monty and Chip, Dale, and Gadget grow into this over the course of "To The Rescue"; although ages are never made explicit, Monty is known to be an old friend of Gadget's father, Geegaw, and the boys don't seem to be much different in age from her. It does help that she seemed to remember him from when she was "knee-high to a knee", though.
* ''WesternAnimation/{{Chowder}}'': Chowder and Gazpacho.
* ''WesternAnimation/TheCrampTwins'': Wayne's (who is around 10 years old) OnlyFriend is a man named Dirty Joe who is well over his 40's. Despite Wayne being a massive {{Jerkass}} toward pretty much everyone in the series, Dirty Joe is the only one he treats with any decency and Joe always enjoys Wayne's company. This is probably due to their similar likes in junk.
* WesternAnimation/DangerMouse, the world's greatest secret agent, and Penfold, his schoolboy-aged assistant.
* ''WesternAnimation/DefendersOfTheEarth'': Mandrake (age unknown but probably in his mid to late thirties or thereabouts) and Kshin (a pre-teen) have this type of relationship. "The Adoption of Kshin", an episode from towards the end of the series, explores how the two of them met and ends with Mandrake formally adopting his young protege.
* ''WesternAnimation/DonkeyKongCountry'': Besides the canon examples of Donkey and Diddy (a young adult and a preteen boy), Candy and Dixie (a young adult and a preteen girl) are shown to have this kind of friendship, right down to seemingly sharing Candy's house.
* ''WesternAnimation/DuckTales1987'':
** Roy (the "Duck in the Iron Mask" from the episode of the same name) is many years younger than Scrooge, but the latter shows great respect to his character and talent, and remembers him more fondly than other people from his past adventures.
** The triplets, Webby, and Doofus Drake are kids and Launchpad is at least in his twenties, but they get along terrifically (although this is somewhat crossed with hero/HeroWorshipper in Doofus' case).
** Scrooge is an old man; Launchpad is still quite young. However, the two do see each other as friends in addition to the boss/employee relationship.
* ''WesternAnimation/DuckTales2017'':
** [[Characters/DuckTales2017DeweyDuck Dewey Duck]], a pre-teen at around 10-11 years of age, is mutually considered best friends with Launchpad [=McQuack=], who is around his late 20s. While this can technically apply for all the kids in relation to Launchpad, none are nearly as close as Dewey is, to the point to where he [[TheDitz sometimes can only remember Huey and Louie as "Dewey's brothers."]]
** Fenton Crackshell-Cabrera, who is likely in around his early to mid 20s, has become really good friends with [[Characters/DuckTales2017HueyDuck Huey Duck]], who again is a pre-teen. Unlike Dewey and Launchpad, who get along super well by both being total goofballs, theses two get along well due to their scientific skills being able to help each other out, whether that be with Gizmoduck tech, or helping out with smaller projects. It's shown in "Dangerous Chemistry of Gandra Dee!" that Fenton actually relies on Huey to help him escape from his tiring hero life as Gizmoduck, and Huey was shown to do what he could to make sure Fenton's date with Gandra went well.
** Downplayed with [[Characters/DuckTales2017LouieDuck Louie Duck]] (as with the other triplets, a pre-teen at around 10-11) and Goldie O'Gilt [[ReallySevenHundredYearsOld (150+)]]. In the episode "Happy Birthday, Doofus Drake!" Louie and Goldie team up in order to con out all of Doofus's money for themselves. Of course, Goldie's ChronicBackstabbingDisorder meant that she had every intent to frame Louie when she had the chance, but she ended up risking her life for him while he saved her from the suffering fate as "Goldie Mama." Even after she ran off with all the money, leaving Louie betrayed, Goldie still decided to keep a photo of him in her wallet right next to her dear Scroogey. It seemed Louie grew on her a little more than she expected. This later pays off during the Fountain of Youth adventure, when it was purely Goldie's fondness for Louie that kept her from running off with the Fountain's water and leaving the Duck family to die.
** While we only see it for one episode, Webby begins a fairly strong friendship with Penumbra after the latter ends up stranded on Earth. While [[ProudWarriorRaceGuy Penny]] has a hard time adjusting to concepts such as having fun and relaxing, Webby manages to get through to her by discussing [[CharacterDevelopment how hard it was for her to adjust to life outside the mansion, and how the triplets had to help her grow as a person]]... and by introducing her to hamburgers. By the end of the episode, Webby has gotten Penny to come out of her shell, and formed a strong friendship with her.
* ''WesternAnimation/FamilyGuy'': [[Characters/FamilyGuyBrianGriffin Brian Griffin]] and [[Characters/FamilyGuyStewieGriffin Stewie Griffin]] are pretty much this considering Brian is an adult dog and Stewie is a baby.
** Herbert and Chris also technically count as this trope (even if Herbert wishes it were more than that).
* ''WesternAnimation/FostersHomeForImaginaryFriends'' has Mac and Frankie, with Mac at 8 and Frankie at 22. Overlaps with a PrecociousCrush on Mac's part.
* WesternAnimation/{{Freakazoid}} and Sergeant Cosgrove. There was even a RunningGag involving Sergeant Cosgrove pulling up to Freakazoid in his car and asking him if he wants to do something together like bumper cars.
* [[LittleMissBadass Noodle]] with all her bandmates from the Music/{{Gorillaz}}, since she joined them at around age 10, while the other three were already adults. They're all clearly more attached to her than to each other.
* ''WesternAnimation/GravityFalls'':
** Twelve year old [[PolarOppositeTwins twins]] Dipper Pines and Mabel Pines are quick to befriend the twenty two year old Soos, a socially awkward {{Manchild}} who works at their great uncle's tourist trap. He is also the one who often accompanies them on adventures.
** Fifteen year old Wendy is also cool with the twins, but the one she really bonds with is Dipper. While this is helped by Dipper having a not-so-subtle crush on the teen, even after giving him the BetterAsFriends talk, Wendy tells him that she has more fun with him than anyone else she knows.
** Also technically applies to Gideon and his [[spoiler: prison gang]], as they are all grown men who follow his orders without hesitation simply because they like him. [[spoiler: Even after they were all pardoned]].
* ''WesternAnimation/HeManAndTheMastersOfTheUniverse1983'' has He-Man and Duncan. Take into account that Duncan is also He-Man's father's advisor/best friend and He-Man's main love interest is Duncan's daughter Teela.
* ''WesternAnimation/JackieChanAdventures'': Jade and Tohru. Many times, Jade would ride the much larger Tohru on his shoulder. She even gave him half of a yin yang necklace to show their bond. On a similar vein, Paco and El Toro Fuerte.
* ''WesternAnimation/{{Jem}}'': This occurs in more than a few episodes. Jerrica and her friends are twenty-something year olds. At least two episodes have them befriending seniors.
* ''WesternAnimation/JonnyQuest'': Jonny and Race have more of a father/son dynamic; however, in one episode of ''[[WesternAnimation/JonnyQuestTheRealAdventures Real Adventures]]'', Race says that Jonny is his new best friend. Jonny's 13/14 and Race is in his late thirties.
* ''WesternAnimation/JoshuaJones'' features one of these between the 20-something title character and the 10 year old Ravi.
* WesternAnimation/KimPossible and Shego ("Stop Team Go"), Shego and Drakken (sometimes).
* In ''[[WesternAnimation/MightyMouse Mighty Mouse: The New Adventures]]'', Mighty Mouse is shown to be close friends with a young orphan named Scrappy.
* ''WesternAnimation/MiloMurphysLaw'': Middle-schooler Milo forms a bond with time travelers Cavendish and Dakota, both adults.
** Cavendish and Dakota themselves possibly fit this trope, since Cavendish sports a grey moustache and acts more grown-up than his (generally) silly partner.
*** [[BeardnessProtectionProgram This may, however, be part of his 1870s disguise]]: the episode "First Impressions" shows both Cavendish and Dakota at their first meeting, and Cavendish looks about the same age as Dakota, if not younger.
** In the Season 2 episode "Spy Little Sister", Melissa becomes the "mentee" of Savannah, a female time agent, and they stop a [[KillerRobot Killer Robot]] together.
* ''WesternAnimation/MinaAndTheCount'' was a series of animated shorts that aired in the ''WesternAnimation/OhYeahCartoons'' variety show about a five-year-old girl befriending a centuries-old vampire. While popular, Nick decided against making it a full-length series and even stopped making the shorts precisely because they were squeamish about the age gap between the characters.
* ''Toys/MonsterHigh'': Draculaura is 1600 years old, Frankie Stein is (when they met) 16 ''days'' old.
* ''WesternAnimation/{{Motorcity}}'': The CoolOldGuy Jacob is this to the teenage Burners. Texas might also be this to the rest of the Burners, as he appears to be out of his teens.
* ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' provides numerous examples:
** The young filly [[KidAppealCharacter Apple Bloom]] and the solitary zebra shaman [[MisunderstoodLonerWithAHeartOfGold Zecora]] bond in "[[Recap/MyLittlePonyFriendshipIsMagicS1E9BridleGossip Bridle Gossip]]" and share both a friendship and an apparent affinity for making potions (although Apple Bloom's, while sometimes successful, tend to have ''disastrous'' results).
** Similarly, there's Scootaloo and [[Characters/FriendshipIsMagicRainbowDash Rainbow Dash]], with the former idolizing and admiring the latter who fulfills something of a sisterly role.
** Both Princesses [[Characters/FriendshipIsMagicPrincessCelestia Princess Celestia]] and [[Characters/FriendshipIsMagicPrincessLuna Princess Luna]] act the most "adult" out of any of the characters on the show, being both in their twenties to thirties emotionally and [[ReallySevenHundredYearsOld at least a thousand years old each chronologically]]. They are also good friends with the main cast. Luna also gets this with the young foal Pipsqueak in "[[Recap/MyLittlePonyFriendshipIsMagicS2E4LunaEclipsed Luna Eclipsed]]".
** [[Characters/FriendshipIsMagicFluttershy Fluttershy]] is also good friends with [[Characters/FriendshipIsMagicDiscord Discord]], who is at least a thousand years older than her.
** In "[[Recap/MyLittlePonyFriendshipIsMagicS8E5GranniesGoneWild Grannies Gone Wild]]", Rainbow is tasked with chaperoning the Golden Horseshoe Gals -- Granny Smith, Auntie Applesauce, Apple Rose and Goldie Delicious, all of whom are portrayed as archetypical octogenarians -- on their yearly trip to [[VivaLasVegas Las Pegasus]]. At the end of the episode, after a series of misadventures and some friendly bonding, the four older ladies invite Rainbow to be a Golden Horseshoe Gal herself.
* ''WesternAnimation/TheOwlHouse'': [[Characters/TheOwlHouseLuzNoceda Luz Noceda]] is fourteen and Eda Clawthorne is, whilst not ''[[YoungerThanSheLooks quite]]'' as [[WitchClassic elderly as she looks]], well over three times that.
** An interesting case from King and [[spoiler: The Collector]], as they, at first glance, may be seen as kids around the same age, but while King is around 8 years old, [[spoiler: The Collector]] is more than four hundred years old ''at the very youngest''.
* ''WesternAnimation/TheRaccoons'': Bert, a young adult, forms friendships with Bentley, a preteen boy, and Lisa, a girl in her late teens.
* ''WesternAnimation/ReadyJetGo'': Jet, Sean, and Sydney, who are possibly in their mid-to-late preteens, are friends with 4-year old Mindy.
* ''WesternAnimation/{{Recess}}'':
** Spinelli, who's nine, and Miss Grotke, who's implied to be in her early 30s. Because of this, Spinelli looks up to her like a mother figure (as Spinelli's real mom embaresses her to extreme levels and forces her into girly activities, which she hates). It's ''adorable''.
** Nine year old T.J. and fifty year old Principal Prickly start off as being each other's SitcomArchNemesis. As the series goes on they find that they're not that different, and it gets brought to a head in the movie, when he and T.J. work together and T.J. learns more about his past.
* ''WesternAnimation/RickAndMorty'' has the eponymous duo. They're [[Characters/RickAndMortyRickSanchez grandfather]] and [[Characters/RickAndMortyMortySmith grandson]], but act more like (very vitriolic, often toxic) friends, complete with Morty being on a FirstNameBasis with Rick instead of calling him "Grandpa". Rick also has this with his granddaughter (and Morty's older sister) Summer.
* ''WesternAnimation/TheSimpsons'':
** [[Characters/TheSimpsonsBartSimpson Bart Simpson]] and Otto.
** And certainly [[Characters/TheSimpsonsLisaSimpson Lisa Simpson]] and the late great Bleeding Gums Murphy.
** As well as Maggie and Moe.
** There's also the VillainousFriendship between the bullies, particularly [[OlderThanTheyLook Kearney]] and Nelson, the latter of whom is the same age as the former's son.
** When Principal Skinner is fired from the elementary school, his FriendlyEnemy relationship with Bart almost instantly turns into a regular friendship, with the two hanging out together after school. There's precedent for it as they formed a bond when Bart [[YellowSashOfPower did a stint as hall monitor]].
** Bart and [[Characters/TheSimpsonsHomerSimpson Homer Simpson]]'s relationship plays out like this in its [[DependingOnTheWriter most positive iterations]].
* ''WesternAnimation/SonicTheHedgehogSatAM'': The [[LaResistance Freedom Fighters]] (most of whom are [[ChildSoldier in their teens]]) have such a relationship with the elderly Sir Charles "Uncle Chuck" Hedgehog. The same could also be said of Tails -- [[InnocentProdigy who is only ten]] -- and the rest of the Freedom Fighters.
* ''WesternAnimation/SouthPark'': In the episode "[[Recap/SouthParkS22E02ABoyAndAPriest A Boy and a Priest]]", Father Maxi forms one with Butters, who sees the PedophilePriest jokes the other adults crack whenever they go to church as no different from the bullying he used to go through at school, and approaches Maxi out of sympathy.
** [[KilledOffForReal Up until Season 10]] there was Jerome “Chef” [=McElroy=], the [[ExactlyWhatItSaysOnTheTin chef]] of South Park Elementary. He’s one of the few adults on the show [[OnlySaneMan that isn’t a]] [[AdultsAreUseless complete airhead]], and one of the only adults Stan, Kyle, Cartman and Kenny wholeheartedly trust in general. They seek his advice for various kinds of situations, and he, in return, won’t hesitate to help the boys out of a jam.
* It's not hugely dwelt upon, but in ''WesternAnimation/StarTrekLowerDecks'', Mariner's ExpansionPackPast, eventually revealing her Academy days were ''over a decade'' before the show's time period, make her considerably older than her fellow Lower Deckers (Tendi is fresh from the Academy, and Boimler has only visited four planets, including Vulcan, when the show starts).
* ''WesternAnimation/StevenUniverse'', besides the MayflyDecemberFriendship some of the gems have developed with humans, has several examples:
** Fourteen-year-old [[Characters/StevenUniverseStevenQuartzUniverse Steven Quartz Universe]] is friends with the ambiguously college-aged Cool Kids, Lars and Sadie, as well as Jamie, who seems to be somewhere in his twenties.
** [[Characters/StevenUniverseConnieMaheswaran Connie Maheswaran]] is a bit shy of thirteen and good friends with Greg, who is around 40.
* Pretty much all Franchise/{{Transformer|s}} - human friendships are like this, due to the near-immortality of the Transformer race (bar accident or murder). It's slightly mediated in the sense that many of them (such as the KidAppealCharacter) [[ImmortalImmaturity have childish personalities]].
** This tends to happen amongst the robot characters as well, due to their [[ReallySevenHundredYearsOld extensive lifespans]]. The [[TrueCompanions main cast]] of ''WesternAnimation/TransformersAnimated'' includes [[ShellShockedVeteran Ratchet]], who fought in the [[GreatOffScreenWar original war against the Decepticons]], Prowl, old enough to have [[DraftDodging tried to dodge the draft]], Optimus, Bumblebee, and Bulkhead, all relatively young, and Sari, who is eight.
** In ''WesternAnimation/TransformersPrime'', the Autobots are [[ReallySevenHundredYearsOld much]] older than their human allies, who have an age range from 12 to 16. Even maturity-wise, the Autobots act like adults (as they've experienced wars) while the human children act their ages.
* ''WesternAnimation/TheVentureBros'': While they're both adults in the present day, Henchman 24 was an adult when he first was recruited by the Monarch. Henchman 21 was recruited/kidnapped when he was 15, and the two were [[ThoseTwoGuys basically inseparable]] until 24's death in Season 3. 21 then became the Monarch's top henchman and close friend, who is about 24's age (or older).
* ''WesternAnimation/TheWackyAdventuresOfRonaldMcdonald'': Ronald [=McDonald=] and Grimace are most likely adults (with Hamburglar and Birdie's ages in this continuity [[VagueAge hard to determine]]), and they are friends with two children named Tika and Franklin.
* ''WesternAnimation/WeBareBears'': 10-year-old Chloe is the three adult Bears' closest human friend.
* ''WesternAnimation/WordGirl'': The title character was once good friends with Steven Boxlitner who was much older than herself. Even though Steven is now the villainous Two Brains, Word Girl still has some sort of friendship with him.
[[/folder]]

[[folder:Real Life]]
* Creator/LauraDern and Creator/ShaileneWoodley (who is 24 years Dern's junior) became close friends during filming ''Film/TheFaultInOurStars'', to the point that Woodley claimed she lived part time in Dern's house.
* Dame Margot Fonteyn and Rudolf Nureyev. Best friends, best ballet partners... and she was 19 years older than him. In fact, Dame Margot was about to retire when they started dancing together, but then she decided otherwise and they were a ballet duo for fifteen more years.
* Music/LadyGaga and Cyndi Lauper. Despite their age difference of 32 years, they get along very well; Gaga considers Cyndi to be a CoolBigSis figure, and Cyndi feels as though she can be as weird as she likes when she's with Gaga.
** Gaga is also friends with Danny Trejo, a 42 year age difference.
** And with Music/EltonJohn (39 years), even becoming the godmother of his adoptive kids.
** And Tony Bennett (''60'' years!), starting when they recorded a song (specifically, "The Lady Is A Tramp") for Bennett's ''Duets II'' CD. It was so well received that they did a whole album together, entitled ''Cheek To Cheek'', released in autumn 2014.
%% * UsefulNotes/RonaldReagan and Brian Mulroney (difference of 28 years)
* While she was in her eighties, Alice Roosevelt Longworth (daughter of UsefulNotes/TheodoreRoosevelt) became friends with forty-something Bobby Kennedy.
* Music/MichaelJackson and either Dame Creator/ElizabethTaylor (difference of 26 years) or Diana Ross (14 years). Jackson was also good friends with Macaulay Culkin (a 21 year age difference).
* Emma Roberts and Jennifer Aniston have a 22 year age gap between them.
* Animal example: A baby hippopotamus that was rescued after floods in Kenya made news everywhere when it befriended a 100-year old tortoise in a wildlife sanctuary.
** Also, a 47-year-old gorilla [[http://tumblr.thedailywh.at/post/19222305842/interspecies-intermingling-of-the-day-samantha-a and a much younger rabbit.]]
** For that matter, Koko the gorilla, and her kitten. Unfortunately, it ended rather tragically.
* When Christopher [=McCandless=], the subject of book and film ''Film/IntoTheWild'', was traveling to Alaska, he briefly stayed with and befriended an old man (given the pseudonym "Ronald Franz" in the book). Franz became deeply attached to [=McCandless=], and prayed for his safety when he left. He became an atheist after Chris's death, believing that any god who would let him die wasn't worth believing in.
* Creator/SigourneyWeaver and Carrie Henn (Newt) became very good friends during and after the filming of ''Film/{{Aliens}}'', despite Sigourney being 37 years old and Carrie only a 9-year-old child.
* Creator/LeonardNimoy and Creator/ZacharyQuinto, the [[Series/StarTrekTheOriginalSeries two]] [[Film/StarTrek2009 Spocks]] with an age difference of 47 years. In fact, whenever they had the time, they would visit each other in Los Angeles and New York. When Zachary heard of Leonard's death, he was in Berlin doing reshoots for a film, so quickly dropped everything to fly back to the States for the funeral.
%% * Basketball star [=LeBron=] James and billionaire Warren Buffet.
* Despite being 26 years older than him, John [=McCain=] was friends with Jon Stewart. Even more impressive considering how different their political beliefs were.
%% * Nikola Tesla and Mark Twain
* Disney star Creator/{{Zendaya}} and country singer Wynonna Judd, with an age difference of 32 years.
* Creator/MaraWilson and Creator/DannyDeVito, as a result of the two appearing closely together in ''Film/{{Matilda}}''.
* Creator/ChuckNorris and Music/JustinBieber. [[http://www.teamliquid.net/forum/viewmessage.php?topic_id=318537 No]], ''[[http://www.justinbieberzone.com/2011/10/justin-bieber-meets-chuck-norris-at-the-set-of-santa-claus-is-coming-to-town/ really.]]''
* Celebrity chef [[Series/DinnerImpossible Robert Irvine]] and his mentor [[ChefOfIron Chef Harold Hillard]]. The latter is 43 years older than the former.
* Conventions, anime conventions in particular, can have these spring up. You're a thirteen year old at your very first con and have no idea where to start or what to do first? Not to fear--if you just ask, some friendly college-aged (or older!) veterans who've done this a thousand times will be happy to show you around.
* Music/WolfgangAmadeusMozart and Music/JosephHaydn were firm friends for decades, in spite of the fact that they were very different people, and that Haydn had several children who were older than Mozart.
* Indie rocker Kristin Hersh of Throwing Muses was friends was 1940s Hollywood actress Betty Hutton for the last two decades of Hutton's life despite a 45 year age gap.
* Thanks to ''Series/{{Arrow}}'', Creator/JohnBarrowman has struck something like this with most of the cast. Being 47, he's over ten years older than Stephen Amell (the lead of the show), and twice the age of Colton Haynes, Emily Bett Rickards, and Willa Holland, yet, going from videos they've made on set, he seems to be best friends with the kids on set.
* Creator/JonahHill is apparently close friends with Creator/DustinHoffman, who even got him a role in ''Film/IHeartHuckabees''.
* From the ''Series/{{Today}}'' show:
** Willard Scott and Katie Couric (difference of 23 years). It's most visible during TheNineties on both said show and the UsefulNotes/MacysThanksgivingDayParade -- he's old enough to be her dad, but they get along like brother and sister. And it is '''adorable'''.
** The same can be said for him and Al Roker (difference of 20 years), who was Scott's successor on ''Today''. Roker says that he learned everything he knows about being a weatherman from Scott, and considers him as a second father because they get along so well.
* Music/KurtCobain and Creator/WilliamSBurroughs. Cobain loved ''Literature/NakedLunch'' and would often keep a copy of the book with him. The two collaborated on a project, ''The "Priest" They Called Him''.
* Bill Mumy and Jonathan Harris. They remained friends ever since they filmed together on ''Series/LostInSpace'', and Mumy even read Harris' eulogy.
* Creator/KatharineHepburn and Creator/BrianBlessed (29 years difference) became friends during filming ''Trojan Women''.
** Also, Katharine Hepburn and Creator/LaurenBacall (17 years difference).
* Creator/GrouchoMarx and Music/AliceCooper (47 years difference), after singing a duet together at Music/FrankSinatra's birthday party. Groucho coined the term "Vaudeville" to describe Alice's style of music.
** Groucho also befriended Creator/BudCort (58 years difference), who stayed at the Marx's home for three years and claims he accidentally swallowed a tooth Groucho gave him as a memento.
* Creator/BrieLarson and Creator/JacobTremblay (16 years difference) became close friends during the filming of ''Film/{{Room}}''.
* Creator/PattyDuke and Creator/DoveCameron, starting when the former appeared on the latter's [[Series/LivAndMaddie TV show]].
* Creator/PeterCapaldi and Creator/JennaColeman of ''Series/DoctorWho'' who, despite a 25-year age gap, struck up an intense friendship that is clearly evident whenever they get together off-screen for interviews and conventions (a prime example being [[https://www.youtube.com/watch?v=mqHMH9pI3eM the 2016 AwesomeCon event in Washington, DC]]). In fact their friendship is so close, and the two are so open about indicating their love and affection for one another - with Coleman directly identifying Capaldi as one of her best friends and Capaldi speaking at length at how unusual it is for two people of their disparate ages to have such a friendship - that a subset of ''Doctor Who'' fandom began to ship ''the actors'', despite Capaldi having been happily married for nearly as long as Coleman has been alive.
* The Creator/Channel4 documentary "Old People's Home for 4 Year Olds" brings children aged 3 or 4 to an retirement village were the producers plan activities in home they will befriend each other. At the start and end of the programme tests are given on their health to see if there is any health benefits for both age groups.
* ''Series/SesameStreet'' puppeteer Carroll Spinney and [[FandomVIP young fan Nick Bertch]], who became friends despite an age gap of at least 60 years. The adorable story can be found [[http://muppetcast.com/show-283/ here.]]
* In his later years, Wyatt Earp developed friendships with actors, William S. Hart and Tom Mix, who both frequently appeared in cowboy movies around that time. When Earp died, they served as pallbearers at his funeral. [[ManlyTears Tom Mix reportedly wept.]]
* Creator/LucilleBall and Creator/CarolBurnett developed a friendship when Lucy showed up to one of her stage performances. Later, when Carol had a TV special, she hesitantly called Lucy to be a part of it, and before she could even get it out, Lucy asked, "What do you want me to do?" After that, Lucy would send Carol flowers on her birthday. Lucy ended up dying on Carol's birthday in 1989, and that afternoon when she heard the news, her flowers arrived.
* At the age of 11, the Dalai Lama befriended Austrian mountaineer Heinrich Harrer, who was 36 at the time. They remained friends until Harrer's death in 2006.
* Creator/ConanOBrien and his assistant Sona Movsesian, with 17-year age gap.
* Creator/JoanCrawford and Creator/StevenSpielberg met while filming the pilot episode of ''Series/NightGallery''. They became friends despite an age gap of at least[[note]]Crawford's exact year of birth is a matter of debate, but the latest date given by sources is 1908[[/note]] 38 years and Crawford's initial reservations about being directed by a twenty-something newcomer.
* Mother Teresa and Princess Diana (50-year age gap) became friends after the latter paid a visit to one of the former hospices, bonding over a shared sense of humanitarianism. Coincidentally, the two died the same week, and Diana was buried with a rosary that had been given to her by Teresa.
* Creator/LinManuelMiranda and Music/WeirdAlYankovic (20-year age gap) are huge fans of each other's work. In 2018 Al recorded "The Hamilton Polka", a polka medley using songs from Miranda's Theatre/{{Hamilton}}, which Miranda was very happy about. Another fun fact: both of them were awarded stars on the Hollywood Walk of Fame for 2018, and they were [[https://www.tiktok.com/@dysequilibrium/video/6947424096145788165?lang=en hanging out together when they got the news.]]
* Music/PaulMcCartney has a knack for making new friends from his connections in the music industry, and that's continued even as he's grown far older than most of his peers. Decades-younger pals of his include Taylor Swift, Kanye West and Dave Grohl.
* Creator/MatthewModine formed a close friendship with Creator/MillieBobbyBrown, with whom he has forty-five-year age gap with, on the set of ''Series/StrangerThings''. Modine has said that he felt protective of Brown and tried to prepare her for fame at such a young age (Brown was only twelve years old when the first season came out and catapulted her to stardom), having known many a FormerChildStar who let the pressures of celebrity get to them, and even lived in Brown's family's guesthouse while filming the first season.
* Crossword designer David Steinberg became friends with puzzle veteran Bernice Gordon when Will Shortz assigned them to collaborate. Steinberg was 16 and Gordon was 99 at the time, and would live to be 101.
[[/folder]]

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