Zevran: You say that like it's a bad thing.
ExamplesPlease stick to examples where the older character is female. Preference for older men is not this trope.
- Kazuki Muto from Busou Renkin has this preference.
- Played with in Hellsing. While Alucard is a centuries old vampre, he still looks rather young. After returning from a rather extendid leave of absence, Integra is around fifty-something. Alucard apparently still finds her attractive. Not that anyone can blame him...
- And then there's his reaction to seeing the Queen again. The fondness in his eyes and his comment that she's even more beautiful as Queen further support this theory. Not to mention it's reciprocated, which implies all kinds of things...
- Very sweetly subverted in Kotetsushin Jeeg. Hiroshi Shiba, the original Kotetsu Jeeg, goes missing for decades, and Michi, his combat partner/girlfriend eventually grows old enough to have a granddaughter. When Hiroshi comes back, having never aged at all (on account of him being a cyborg), Michi sadly tells him that she feels ashamed that he has to see her like that. Hiroshi answers that he doesn't care, because he'll always love her just the same. D'AWW!!!
- Rizelmine manages to diffuse a bit of its bizarrely over-the-top lolicon bait Genki Girl by giving its male main character this trait... which, due to her being an Android that age-regressed to lolicon bait actually gave the main character his fetish when he was younger.
- Mizuiro, one of Ichigo's classmates in Bleach, has a stated preference for older women, which sets up for a moment where Ichigo tells Rukia to stay away from the boy, much to Mizuiro's confusion.
- Mahoraba, at least the manga.
- The Electric Tale of Pikachu has Ash in the manga in love with Gary's older sister, Daisy. In the Pokémon animé, Brock pretty much defines this trope, as he instantly falls in love with the Character of the Day girls, but only if they're either around his age or older, particularly Professor Ivy, and any and all Nurse Joys and Officer Jennys.
- In Love Hina, one of Keitaro's two childhood friends, Masayuki Haitani, displays an ongoing infatuation with the series's Christmas Cake, Haruka.
- Marie in Haré+ Guu was worried Haré might be one of these.
- Played with in Star Driver. In it, we have Tsubasa, who is the only guy in all of Southern Cross High that isn't attracted to Hina, the supposed "new girl", because he has a crush on Midori Okamoto, the school nurse... who happens to be the true identity of Hina and a notorious lover of Bishounen.
- Mahou Sensei Negima!
- Negi might fit into this, as all the girls he could potentially have a romantic interest in are older than he is, usually by a margin of four or five years.
- His father, Nagi also appears to be a bit younger than Negi's mother Arika. Her age hasn't been confirmed, but she sure looks older than he is, and her only known relative (Asuna) is definitely Older Than She Looks (Chapter 284 reveals she is at least a hundred years old).
- When asked if the reason he drew cute teen female characters all the time was because he was attracted to them, series creator Ken Akamatsu stated that his preference is actually older women. He's just really good at drawing cute young girls...
- Please Teacher!
- This anime could be an example, however one wouldn't tell Mizuho is actually much older than Kei. According to a Newtype magazine centerfold, she's twenty three when she shows up on Earth. She is an alien from outer space and he has spent three years in a strange sort of coma..
- And also, the friend of Kei's who pursued their female classmate who suffers from the same sort of strange coma-disease, and admits out loud that he has a fetish for women who are older than they look.
- Yu-Gi-Oh!: Jounouchi and Mai, who is 8 years his senior, are widely regarded as "the only popular heterosexual couple in Yu-Gi-Oh!." That pairing is Serious Business. When one author revealed in his Continuation Fan Fic that one character (established as Jounouchi's daughter) was the daughter of Jounouchi and Rebecca, the readers were not amused. His next story promptly returned to Jou/Mai.
- Like just about everything else in Yu-Gi-Oh!, this age difference was brought up and made fun of in Yu-Gi-Oh! The Abridged Series.
Joey: But you're ten years older than me!
Mai: I know. Creepy, isn't it?
Joey: (aside to the audience) Actually, this is the closest thing this show has to a normal relationship.
- Like just about everything else in Yu-Gi-Oh!, this age difference was brought up and made fun of in Yu-Gi-Oh! The Abridged Series.
- Hawk's Eye of Sailor Moon's Amazon Trio, who specifically targets older beautiful women. One of them is Ikuko Tsukino, Usagi's mother.
- Akira Mimasaka from Hana Yori Dango. Maybe Rui, since his long-time love interest Shizuka is actually older and more mature than he is.
- 14-year-old Yoshimori in Kekkaishi has his eyes set on his 16-year-old childhood friend, Tokine. Later in the manga, he saves another girl of similar age from a high fall and she briefly becomes his Stalker with a Crush. These may contribute to an observation a regular acquaintance makes about Yoshimori's romantic preferences: "You like older girls."
- In the anime adaptation Masamori, Yoshimori's older brother, makes the same observation to tease Yoshimori: "You sure like them....mature."
- Not to mention that he also likes cake, leading to the inevitable puns; a cake-baking, cake-loving, cake eater. Cake is his LIFE.
- Parodied in The Prince of Tennis: Takashi Kawamura is mistaken for someone who Likes Older Women by his school friends when he was seen talking to a beautiful older woman. Turns out she was the mother of an old friend of his and their talk was not a romantic one: she was asking him to help with her rebellious son.
- In You're Under Arrest!, Shouji Tokairin for Natsumi. Tokairin is some years younger than Natsumi... which makes him someone who Likes Older Women.
- In Ikki Tousen, people think Kakouton (Xiahou Dun) is one of them, specially when they meet Hakufu's mother Goei (Lady Wu) and she flirts with him. He isn't amused.
- Zettai Karen Children's Kaoru Akashi, not even out of elementary school, is already very open about her love of older women, which spills over into her having some Lovable Sex Maniac tendencies.
- Parodied in Azumanga Daioh, when a guy asks another whom he likes better, Yukari or Nyamo. This guy, seeing Yukari around and overhearing, answers "Yukari, of course", and the other replies "You have a warped taste in women", and gets promptly whacked by Yukari.
- The trope is inverted with Wataru in Hayate the Combat Butler. It seems older girls (although the gap between him and Sakuya or Aika is pretty small, they're still older) are more actively interested in him, while his moments of interest in any of them don't happen as frequently. Although recently he has his maid Saki in mind.
- From WORKING!!, Yachiyo is a lesbian (or Single-Target Sexuality) version. She quite openly crushes on Kyouko.
- Garcia Lovelace from Black Lagoon. And the guy is bold enough to pull a surprise kiss on the target of his feelings◊, his Mama Bear, Roberta.
- The main character, Akira Inugami in Wolf Guy - Wolfen Crest for his Hot Teacher.
- In Mermaid Melody Pichi Pichi Pitch, Nagisa is one year younger than Hanon (who was in love with her music teacher, before he went away in the second season). Even though Hanon yells 'I only like older men!' to try to prevent Nagisa from flirting with her, he ignores it and flirts with her anyway. She gives up later and date him at the end of the story...
- In Kimi Wa Petto, 18-year-old Momo is pretty open about his crush on his 29-year-old benefactor Sumire. They end up Happily Married in the epilogue.
- Please Save My Earth The age differences of the two main leads are obvious. This is actually understandable considering Rin Kobayashi is reincarnated 9 years later than Alice.
- Unbalance × Unbalance is a good example for of this, between Jin-Ho Myung and Hae-Young Na, not to mention Hae-Young is Jin-Ho's teacher (respectively renamed as Kenichi Kando and Elina Takanashi in the japanese version).
- Every male in Freezing is this. Generally senior females in the school would desire younger males to be their partners. This is due more to the fact that their powers seem to work better when the Pandora is older than her Limiter - usually by a year.
- Shinpei from Wandering Son saw the protagonist with an adult friend of his and started becoming the characters friend in order to meet that women. His love for her went away after he learned she was Transsexual though.
- From Ano Natsu De Matteru. It must be Love at First Sight for Kirishima Kaito but his alien love interest Ichika Takatsuki here is at least 2 years, if not, much older than him.
- It'd be a stretch to say that Light likes older women, but he seems to "associate" with older women. His canon "love interests" are about a year older than him.
- It's hinted that Matt had a crush on Misa while he was spying on her. Even though he thought she was about fourteen or so, she was five years older than him.
- Deadpool openly lusts after Bea Arthur. In one issue he lusts after Spider-Man's Aunt May, sighing how she's "so like my Bea." All members of Weapon X, mutant or not, have a slow aging factor, and Deadpool is cursed to be unkillable, so he may have grown up in the same era as Bea Arthur. When Deadpool actually died, he got together with Death herself. Her on-and-off boyfriend Thanos angrily brought him back to life and made him immortal to separate them.
- The true love and soulmate of Chris Kent is Thara Ak-Var, a childhood friend of Supergirl. Fortunately, Chris underwent a Plot-Relevant Age-Up from a little boy to a Bishōnen Chick Magnet of similar age to her.
- By contrast, in Love and Capes, CM Expy Major Might starts a relationship with Wonder Woman Expy Amazonia; in his Superpowered Alter Ego, he looks like an adult (and she is one), but he's really 10 years old. Amazonia is not best pleased to learn this. Of course, she's on the rebound from the main character, the Crusader, and the Major is a huge fan of her ex (to the extent of choosing to have the same powers so that he can be like his hero), so it's a valid question as to whether Amazonia is being a bit of a Mrs. Robinson here.
- Subverted in Captain Atom with Sally Starshine. She certainly looks much older than Cameron Scott, but since he jumped eighteen years into the future, they are actually contemporaries, which is one of the reasons he is drawn to her. Also, it should perhaps be noted that Cameron started dating his first wife, Angela, when he was a junior in high school and she was a senior.
- Buffy the Vampire Slayer: Buffy is this in the comics. Buffy, who has been a Slayer for at least ten years, is the romantic interest of the much younger Satsu. Despite not being gay and not wanting a relationship Buffy sleeps with her. Twice.
- A Pleasant Surprise features this prominently. It's not stated exactly how old Fluttershy and Midnight are, but it's more than enough difference to qualify.
- Fobbies Are Borange: Jeff "I am so ready to eat your cake" Andonuts is this in every sense of the word. Possibly Lampshade Hung due to the first person he falls for being named the Magic Cake Lady.
- Racer and the Geek by Kalash93 makes this for the protagonist and ALL his possible love interests.
- By the same author and featuring the same characters, Welcome to the Brothel and Relax set up this dynamic between the protagonist and his love interest, with one rare twist: she's a local prostitute and he's a foreign volunteer fighting in her country's civil war.
- In Child Of The Storm, Clint has the trope specifically name checked by Natasha. He doesn't deny it. Evidence for this stacks up when you note that he's 28 and has dated Wanda Maximoff. Who would likely have been at least in her late thirties at the earliest when they hooked up (even if she doesn't look it) and has a child half his age. He's also got a thing for Natasha, but let's face it, who doesn't.
- Harry's got a minor variant on this - he's got a thing for older women, but being surrounded by the likes of Natasha (who he has decided confused feelings about since she treats him like a nephew), Sif, Darcy and Carol (who may only be a year older than him at most, but looks rather older than that), is going to make this kind of inevitable.
- Uzumaki Naruto is often depicted as a cake eater in fanfiction. Anko, Ayame, Konan, Kurenai, Shizune, Tsunade, Mei, Kushina, Koyuki, Tsunami, etc.
- Twilight Sparkle in Dash's New Mom, which was one of the reasons she started courting Blue Streak. Blue Streak is Rainbow Dash's father, and Dash is the same age as Twilight, and said daughter is very creeped out by the two's romance.
- Noriaki Kakyoin from Jojos Bizarre Adventure made one comment about his ideal girlfriend being like Holly, Jotaro Kujo's mom. Memetic Flanderization has made him into an insatiable MILF hunter who wants to do every hot mom he comes across.
- Dodger for Tangerine in The Garbage Pail Kids Movie. Until Juice sends the eponymous kids to the State Home for the Ugly.
- The movie Cougar Club is entirely about this.
- Aram falls for Sandy, 15 years his senior, in The Rebound.
- Mystery Men: Dr Heller (Tom Waits) cruises retirement homes "for the ladies".
- Invoked in Indiana Jones and the Temple of Doom, when Willie Scott thinks the Maharaja of Pancot Palace has been showering her with gifts, and then:
Willie: That's the Maharaja? A kid?!
Short Round: Maybe he like older women.
- American Pie: Finch has a distinct preference for older women. (most specifically, the mother of one of his friends). Despite becoming a bit of a Kavorka Man in the 2nd film, he always found women his own age wanting for one reason or another.
- In Don Jon, Jon (Joseph Gordon-Levitt) hooks up with Esther (Julianne Moore), who is much older than him.
- In A Brother's Price, Jerin mentions having had a crush on his teacher, and later falls in love with a woman who is about ten years older than he.
- In Dragon Bones, Beckram is called out by his brother on the fact that he has an affair with a woman who could be their mother, age-wise. His defense is pointing out that she's very beautiful, which the brother must grudgingly admit, is true. His brother also complains that he's been hearing sex noises from Beckram's room since they were teenagers and Beckram seduced their mother's lady-in-waiting, who, presumably, was their mother's age, so that seems to be a habit.
- Tommy Flood in Bloodsucking Fiends (19 years old), as demonstrated by the fact that he's willing to immediately shack up with a woman seven years his senior.
- In Florence Barclay's novel Through the Postern Gate the lead male is a Bunny-Ears Lawyer Ace Pilot named Guy ""Boy Blue" Chelsea, who is a Dogged Nice Guy for the 10-years-older Hot Librarian Christobel Charteris. In fact, Christobel cites the age difference as the reason why they should not date.
Christobel: "When I met you, you were six. I was 16".
- Zar-bettu-Zekigal, from Mary Gentle's Rats and Gargoyles, explicitly prefers older women (shortly after she's first introduced, she starts rhapsodizing over her fortyish landlady Evelian's laugh lines). When she later becomes infatuated with the Hyena (who's only got about ten years on Zari), it mystifies her that she's crushing on someone so young.
- Stephen Colly in I Capture the Castle ends up having sex with Leda Fox-Cotton. Movie-wise, all they do is show her playing with his hair late at night, but you know what's happened.
- In Bridget Jones: Mad About the Boy, Bridget (51) dates Roxter (30), who enthusiastically talks about how great it is to be with a "cougar." Bridget's friend Talitha is 60 and seems to attract similar guys.
- Eddie in A Widow For One Year by John Irving. He has an affair with a woman at least 20 years his senior (he's 16 in the first part of the book) and always prefers much older women. Taken Up to Eleven by the time he's over 50 and attracted to women in their 70s.
- Buffy the Vampire Slayer: Xander Harris harbors an unspoken desire for Joyce Summers. He's a conquistador! And for some Sunnydale High teachers as well. And Anya, who is 1120 years old.
- In Smallville, it is a one episode thing, but they had a little Flight of Romance so it is worth a mention. Warrior Angel, who is actually only 12 years old, is obviously attracted to the then-about 23 Chloe Sullivan.
- Richard Fish, in Ally McBeal, actively goes after older women because he has a fetish for the folds under a woman's chin that build up as she gets older. He wound up marrying a woman who was ten years younger than him, but many fans prefer to pretend the last season didn't happen, so... you know the drill.
- Noah "Puck" Puckerman states this as the sole reason for joining Acafellas and performing at the PTA meeting.
- Also, Josh Groban's character.
- Boston Legal, 40-ish Alan Shore competing with Denny for the 60-ish Shirley Schmidt. (Neither wins.)
- Carter on ER wasn't really one, but was accused of it after dating a couple of older women.
- Lie to Me: One episode revolves around a widow of a much younger man. After the team loudly derides the age gap, Torres says that she's been in a relationship with an older partner, and it was healthy and fulfilling. This is an example of Likes Older Women because the older partner was a woman.
- Friends: Frank Jr. just doesn't care if his wife is twice his age.
- He's the only character who actually married his older love interest, but there were other instances in the show, like Elizabeth and Ross, or Monica and Richard. Or Monica and Young Ethan (TOW The Ick Factor.)
- Connor from Angel. Apparently, his profound love of Christmas Cake is so deeply a part of who he is, changing his memories and personality doesn't make it go away.
Connor: I guess I've always had a thing for older women.
Angel: They were supposed to fix that.
- Doctor Who
- The 2010 Christmas Special does it both ways. In the same relation. Abigail Pettigrew (age unknown, but adult, probably in her twenties) is held in stasis by (initially) Kazran Sardick's father, as collateral for a loan. While Kazran is a young boy, The Doctor briefly releases her. By the time Abigail is put back in stasis, Kazran promises they'll be back every Christmas Eve. They do so, and while Kazran is still younger than Abigail, they 're mutually attracted to each other. Until one Christmas Eve, Kazran learns Abigail has only one day left to live, and he decides to not release her on following Christmas Eves. Eventually, Kazran becomes an old (and grumpy) man. And on a Christmas day, Abigail is the only person who can save the day. Old enough to now be her grandfather, Kazran releases Abigail. Of course, they still love each other.
- While the Doctor himself doesn't count, being over 900 years old, they do seem to like using this dynamic ever since they hired the twenty-something Matt Smith. Almost every quasi-flirty relationship has been with a character whose actress is at least a little older than him. There was Queen Liz X (both she and her actress Sophie Okonedo were 40,) River Song (whose actress Alex Kingston was born in 1963) and Idris (who was played by an actress in her early 30s, but was dressed in a Victorian getup that made her look a little older.) He gets in a Mrs. Robinson joke about River just to make the point.
- Several Korean Series play this trope up:
- What's Up Fox?: Nine years separate Byung Hee at 33 from her boyfriend Chul Soo, 24, whom she used to help babysit. He announces he's liked her since practically puberty.
- Flower Boy Ramyun Shop: Chi Soo's a senior in high school; Eun Bi's a 25 year old student teacher.
- Oh My Lady: The young K Pop Idol Singer falls for the over-30 divorced mom.
- Hanto in Engine Sentai Go-onger, whose crushes have included Kegareshia (played by a then 27-year-old actress) and Miki from Juken Sentai Gekiranger (in her 40s and married with a daughter.) He is 16.
- The 8-year-old brother of a patient on one episode of House gets a crush on Cameron.
- The Benny Hill Show: Benny Hill as "Dapper Dan the lady killer man" sings a song in praise of having an older woman lover:
They don't yell, and they don't tell, and oh, they're grateful as hell,
So give me an older woman every time.
- Played for laughs on New Tricks (note: the premise of the series is that retired police officers are brought back to the force to serve as consultants on cold cases, and much of the humor is based on the ensuing Values Dissonance):
Brian: Remember Hans and Lotte Hass on telly when we were kids?
Gerry: Oh-ho! I never missed that programme.
Brian: You were hooked on diving?
Gerry: No, no. It wasn't that. No... well, this was the Fifties. It was the only show on TV where you could see a fit bird in a swimsuit.
Sandra: How old were you, Gerry?
Gerry: Dunno. Nine? Ten, I suppose. (disapproving stares) Yeah, I've always had a thing for older women.
Sandra: (deadpan) Now there aren't any.
- Neil Sutherland of The Inbetweeners is this, losing his virginity to a woman at work, lusting after Will's mum, making a move on Miss Timms and shagging Anything That Moves on holiday. The other lads have to physically restrain him from going off with another older woman on holidays. Will is this to a lesser extent as well.
- In one episode of Doc Martin, a painter has the hots for Auntie Joan. Martin suspects an Oedipus Complex, and it's later revealed that he's grieving for his dead mother ...
- One character in The Catherine Tate Show was Ali, who ruins social situations with unknowingly tactless remarks. In one sketch she meets a young 20-something man who tells her about his plans to go on a vacation with the middle-aged Polly. Ali replies "I wouldn't go on holiday with my mother!" but then discovers Polly is actually the man's girlfriend.
- In the Japanese drama series Last Cinderella, Hiroto (25) falls for Sakura (40) and she chooses him over another man closer to her own age.
- Jeremy Gilbert on The Vampire Diaries. His three love interests have been Matt's older sister Vicki, his older sister Elena's best friend Bonnie, and Anna, a vampire who is hundreds of years old.
- Ricardo Arjona's song "Señora de las Cuatro Décadas" (Lady of the Four Decades) is written from the POV of someone who Likes Older Women who tells his much older girlfriend to not try make herself look younger than she is, since she's perfect for him already.
- In the music video of Toby Keith's "You Shouldn't Kiss Me Like This (Unless You Mean It Like That)" a eighteen/nineteen yr old boy has a vivid daydream of he and his older female employer falling in love and making love with one another. Unfortunately or fortunately for him, her real personality is vastly different from his fantasy of her, and she seems to barely recognise his existence.
- Emmanuel's song "Bella Señora" (Beautiful Lady) is a subtler example, as the lyrics don't openly state that the man is one of these but has some verses about the "lady"'s skin not being "porcelain-like" like in the past.
- Elton John's "Teacher I Need You."
- Rod Stewart, "Maggie May."
- Ronnie McDowell's "Older Women (Are Beautiful Lovers)".
- Garth Brooks' "That Summer"
- The Bare Naked Ladies song "Maybe Katie" is about how the singer doesn't care about the fact that his girlfriend is older than he is.
- "Summer: The First Time" by Bobby Goldsboro.
Just because her youth is fading,
Doesn't mean she's not worth dating.
- Hailing from Brazil comes "Panela Velha" ("old pot"), with the immortal chorus "it doesn't matter if she's older! Old pots make the best food!"
- Rick Wakeman, Progressive Rock keyboardist of Yes, The Strawbs and several solo projects, once made this joke to his audience while in his 60s: "When I was younger, I used to have a thing for older women... Not any more!"
- Persona 3
- Kenji, one of your classmates, loudly proclaims his love for one of the teachers in Gekkoukan High School, and devises a Zany Scheme to get her to fall in love with him. It's Played for Laughs at first, but as Kenji's Social Link progresses, it becomes increasingly clear that he is at best heavily in denial as to the reality of the situation. It becomes even harsher in the female protagonist's route, which introduces Kenji's Unlucky Childhood Friend Rio: she's had feelings for him to ages, but he's too caught up in his attraction to his teacher to notice.
- The female protagonist is the object of a crush from Ken Amada, which you can pursue.
- The male protagonist can also pursue a relationship with an older woman he meets over an online game. She turns out to be his homeroom teacher at the end of the game.
- Takumi from Battle Moon Wars openly admit his preference in his conversation with Aozaki Touko, which kinda explain why he is unfazed by cast of three five galge games around him.
- In Tales of Symphonia: Dawn of the New World, there is evidence that Lloyd has become one of these, if Colette is not chosen. Also adding at one point in the game, Lloyd admitted that he is more fond of older woman referencing the time when he actually proposed to Paul's mother Lilia.
- Sonic the Hedgehog has Amy Rose who's 8 (but had a Plot-Relevant Age-Up wish so she would appear 12), in love with Sonic the Hedgehog who's 15. To a degree, Knuckles the Echidna who's 16 has in canon been shown to have a soft spot for Rouge the Bat who's 18. There's also Vector the Crocodile, who's 20 and has a crush on Vanilla the Rabbit who's at least several years, if not a decade his senior. Not that you would be able to tell any of this by simply looking at the characters. They sound, look and act like a group of fraternity 20-somethings.
- In Dragon Age: Origins, Zevran seems to like hitting on Wynne even more than hitting on the PC as every conversation he has with her involves either sex, her breasts, or both. He might just be messing with her, but knowing Zevran, he probably wouldn't object if Wynne responded positively to his advances.
- In Fire Emblem, there are a few example.
- In Fire Emblem Elibe, Roy, has 6 possible wives: one is Cecilia, a visibly older woman who was Roy's teacher in combat and tactics.
- In Fire Emblem Tellius, Boyd, 19, says to Titania, who is 41 or so, that he always had a crush on her. And when Titania questions his logic, Boyd says his judgement was assisted by the fact that Boyd was sure that Titania was younger than HIS mother, who is also the mother of Oscar, whose age is 24.
- Every one of Dew's potential wives is several years older than him except for Sylvia (she's said to be 14 in the games and 16 in the Oosawa manga) or Raquesis (said to be 16 in the mangas).
- Fire Emblem Awakening has Ricken. Being the youngest member of the Shepherds, almost every one of his potential wives is older than he is.
- In his C-rank support conversation with Nowi, Gaius states that he likes older women because they have a certain degree of maturity.
- Also Donnel, while he is slightly older than Ricken, like Ricken, his youngest potential love interest (Lissa) is older than he is.
- Otacon in the Metal Gear Solid series, played for drama.
- Toby in Catherine has a crush on Erica, an old friend of the main character, who is 32. However, in the True Lovers ending, he learns that she is a post-op transsexual.
- An option in Mass Effect 2 to play Shepard as one, featuring Samara as the cake, who is several hundred years old (even accounting for her race's life expectancy, she's old enough to have three daughters, one of whom can pass off as her) as opposed to Shepard, who, as of Mass Effect 2, is either 29 or 31 (depending on whether you count the two years (s)he was dead)... although (s)he gets turned down because Samara is married to her job.
- Jude from Tales of Xillia, has once said Milla is attractive and commented on how Presa was "cute". When Alvin jokingly asks if Jude likes older women, Jude responds with an embarrassed chuckle and says "I don't know. Maybe."
- Trevor in Grand Theft Auto V. The only women he hits on are older than him. This is despite the fact that he's in his late-40's/early 50's.
- In Tales of Graces, Hubert, who is around 17-18 years old, has a pretty obvious attraction toward resident Cloud Cuckoo Lander, Pascal, who's 22.
- In Assassins Creed III in the first Sequence of the game the player can have a conversation with Benjamin Franklin in which the latter explains the "benefits" of courting a older woman
- CLANNAD's canonical plot goes with Tomoya falling in love and marrying an older girl. His wife Nagisa is only 1 year older than him, though. Another route can have him fall for Misae, his landlady, who seems to be in her mid 20's.
- Maji De Watashi Ni Koi Shinasai
- Our protagonist here admittedly stated that he prefers older women during one the main routes. Overall he has 2 candidates to fill this trope in the original game one of which is his homeroom teacher
- In addition he gets about 5 more potential older partners in the expanded sequel Majikoi S. 2 of the 5 were more or less extras though.
- In Crescendo you have the choice of either your older non-blood related maternal sister Ayame or your smexy aloof, Christmas Cake school nurse Kaori, Take your pick.
- In Jewel Knights Crusaders your hero is currently in high school and there are 2 candidates that fulfill this trope. One is a hot nurse who is also currently attending college, another is a childhood friend who the hero frequently call Onee-san.
- This appears to be very common in dating sims, usually with a sempai.
- Skwisgaar of Metalocalypse has a preference for 60+ year old female partners. And overweight ones too. G-MILFs, in his own words. In addition to the MILFs and Soon-to-be-MILFs.
- Generator Rex has Rex who has a crush on Dr. Holiday, who is at least a decade older than him.
- J'onn J'onzz was seen with a middle-aged woman, disguised as a middle aged man in the finale of Justice League Unlimited. Given the brief look between them before he returned to his original form, it seemed he'd already revealed his identity to her and she was okay with it. Given that he was Really 700 Years Old and had been married before, its no wonder he'd go with someone more mature, at least by earth standards.
- In The Spectacular Spider-Man, sixteen-year-old Peter Parker very publically proclaims his interest in twenty-year-old secretary Betty Brant, and plays the Dogged Nice Guy to pressure her to be his date for the High School Dance. He is thwarted by his Aunt May, who approaches Betty for a frank talk about their relative ages. Betty then turns Peter down.
- Spike is this for Rarity in My Little Pony: Friendship Is Magic. Admittedly, this example is somewhat muddied in that Spike, despite being a baby dragon, is actually not much younger than the adult main cast and is really only considered such due to dragon's centuries-long lifespan. He does consistently behave less mature than the rest of the cast, though.
- Aang from Avatar: The Last Airbender has a crush on Katara, who is a about two or three years older than he, even though he's chronologically 112 years old. As it would turn out in later installments in the series, They Do.
- Sokka, a fifteen-year-old, even took an interest in the princess of the Northern Water Tribe who turned sixteen upon the main characters' arrival.
- Parodied in Codename: Kids Next Door with King Sandy. He's into older women... though being about 7 years old, that means said women (like Numbuh Three) are 10.
- Phineas and Ferb: Ferb towards Vanessa, who is most likely 4-5 years older than him. Due to certain bits of Word of God regarding Phineas' future relationships, this might also apply to him as well since it is widely suspected that Isabella is older than he is.
- Young Justice
- Wally, who has flirted/commented on the attractiveness of several women older than him, most notably Black Canary. He eventually winds up with Artemis, though.
- Dick is a subtler example: the tie-in comic shows that by season two he's had relationships with Zatanna, Rocket and Bette Kane. All are older than him, though only by a year or two.
- This is a common idea in just about any variation of the TMNT comics. No specific age is given for the female characters, but they're all most likely in their later teens or twenties. Obviously, the main characters are teenagers, but where they are in their teens depends on the writers.
- Gravity Falls has two with a 3 year age gap between Dipper and Wendy (12-15) and Li'l Gideon and Mabel (9-12).
- On Daria, Upchuck by no means limits himself to any one kind of girl, but when he realized the supposed high-schooler he was flirting with was actually Brittany's stepmom he suddenly becomes a lot more interested.
Upchuck: An older woman. A younger, willing man. Do I dare to dream? Please, don't be gentle. (notices Brittany's stepmom has walked away) Huh?
- The Simpsons: Most of Bart Simpson's love interests are noticeably older than he is. There's also plenty of romantic subtext between him and Edna Krabappel, as well as one episode with a child therapist that was played out just a little too straight.
- Voltalia is currently in a relationship with Starcharter-75, who is four years her junior.
- Azrael of Gaijin Smash has confessed to being one of these on a few occasions.
- Aaron Johnson and Sam Taylor Wood take this Up to Eleven, at this time of editing they're 20 and 43 respectively, and have a child together to boot.
- Comedian Louis C.K. has stated his preference for "women women" hardened by maturity and maternity, as opposed to "girls" who haven't experienced motherhood.
- The then 20-something Harry Hamlin met the then 40-something Ursula Andress on the set of the original Clash of the Titans and fathered her only son.
- Ashton Kutcher married Demi Moore. (Although, they did get divorced.)
- Brock Lesnar's wife, Sable, is ten years his senior.
- Speaking of wrestling, Mickie James is eight years older than her partner, Magnus.
- William Shakespeare was 18 years old when he married a local woman named Anne, who was 26. For a young man to marry a reasonably older woman was in fact rather unorthodox. It may have helped that she was three months pregnant with his child when they got married.
- Dev Patel is dating Freida Pinto, who is 5 and a half years older than him.
- Hugh Jackman's wife and fellow actress Deborah is 13 years older than him.
- Scottish Actor James McAvoy married Anne-Marie Duff when he was 27 and she was 36 while working together in the tv drama Shameless.
- Chris Hemsworth of the Thor film married Spanish actress Elsa Pataky, who is 7 years his senior.
- Ralph Fiennes, born in 1962, left Alex Kingston, born in 1963, for Francesca Annis, born in 1945. Bene Gesserit witchcraft !
- Justin Timberlake is about 8 years younger than his ex Cameron Diaz.
- Nick Cannon married Mariah Carey, who is 10 years his senior.
- Dr. Reza Jarrahy husband of Geena Davis, 15 years older than him. They have three children.
- The late Heath Ledger was 18 when he lost his virginity to then 36-year old Roar co-star Elizabeth Pena, and later had relationships with Heather Graham, who was 9 years older than him, and Naomi Watts, who was 11 years older.
- Naveen Andrews of LOST. He caused a minor scandal at the age of sixteen when he fell in love with and moved in with his math(s) teacher; they later had a son. He next had a long-term relationship with Barbara Hershey, 21 years his senior.
- Benjamin Franklin, who wrote an essay extolling the virtues of older women as mistresses.
- Sam Kieth, comic book writer and artist and creator of The Maxx, is about 20 years younger than his wife, whom he first met when he was 15.
- Tony Parker, a French professional basketball player, also ex-husband to Eva Longoria of the famed tv show Desperate Housewives to which he is her junior by 7 years.
- Japanese actor Kenichi Matsuyama, best known for playing L in the live action adaptation of Death Note is married to Koyuki Katō who is older than him by 8 years, not including the months.
- Voice actresses Megumi Ogata and Chisa Yokoyama are both married to guys like these. Ogata's husband is 13 years younger, Yokoyama's is 11 years her junior.
- John Lennon was 7 years younger than Yoko Ono.
- Steven Strait is married to Lynn Collins, who is 9 years his senior.
- Harry Styles of One Direction.
- Over the last several years, MILF/Cougar-themed pornography that features women who are in their 30s and 40s (or at least appear to be that old) has seen a steady increase in popularity, to the point where it's now one of the most popular categories of porn.
- Porn star Lisa Ann, who specializes in MILF/cougar porn, is currently the most searched-for porn star on the web.
- Country music star Marty Stuart met singer Connie Smith when he was 12 and she was 29. He promised himself that he would marry her someday, and he did.
- Nick Jonas is dating Delta Goodrem, who is 7 years his senior.
- Shakira is married to Spanish footballer Gerard Piqué, 10 years her junior. Which is also an Older Than They Look case, since they look approximately the same age. They also have a son together.
- Swedish football superstar Zlatan Ibrahimović has been in a relationship with former model and children's TV presenter Helena Seger, 11 years his senior, since 2002. They have two sons together.