May–December Romance

"Some say I'm robbing the cradle, but I say she's robbing the grave!"

— Hubert Farnsworth, Futurama

It refers to a romantic relationship where there is a drastic difference in age between the two participants.

These seem to be less common in modern media, perhaps because some now perceive them to be Squicky. However, they still crop up from time to time; they're very common in soaps in particular.

The ways in which these relationships can occur in media can vary:

• Teachers and students. (The teacher must be significantly older than the student.)
• Lover and Beloved. (The mentor can't be very young themselves to count as an example of this trope.)
• An Arranged Marriage between two people of different ages that leads to real love.
• If an Older Sidekick or Battle Butler develops a Bodyguard Crush on their younger ward.
• If a writer is Pairing the Spares or Cleaning Up Romantic Loose Ends, they may pull a Last-Minute Hookup between two odd characters from two different generations.
• If the Dirty Old Man or Dirty Old Woman somehow manages to score.
• A plot to get in the older partner's will, or control the older/younger partner's estate.
• A person who Likes Older Men and/or Likes Older Women getting the attention of their love interest.
• A man who takes a much younger and prettier Trophy Wife or mistress.
• Or, hey, maybe the two characters just met and hit it off.

Generally, the man is the "December" (elder) and the woman is the "May" (younger), though it can happen the other way around. This can sometimes be a Double Standard in Hollywood, as while older actors get paired up with younger actresses, it doesn't happen so often in reverse.

May lead to cases of Ugly Guy, Hot Wife if the years haven't been kind to him. This is the romantic version of the Intergenerational Friendship.

It is the Real Life, mundane version of the Mayfly–December Romance and the Sub-Trope and extreme version of Age-Gap Romance.

Due to continued confusion over the applicability of this trope, here are the criteria that need to be satisfied to qualify for inclusion here:

• Presuming normal human lifespans, the partners must be at least 25 years apart in age and at different stages of life. Presuming normal human lifespans, the older needs to be at least 50 and of a senior citizen age. Similarly, the younger can be no more than 35, because the younger one is in the spring of their life.
• The ages are from when the relationship started. If a 50-year-old and an 85-year-old are a couple, this trope would qualify if they've been together for 30 years, but not if they started dating last week.
• Age is based on time actually living. Time spent frozen or otherwise in a suspended state is irrelevant. If a character goes into suspension at age 30 and comes out 100 years later, they're 30, not 130, for the purposes of this trope. Time travel also does not count, for example, a romance between a contemporary and a person of similar age but born decades in their future. An arguable exception is if said time traveller falls in love with someone from decades past, returns to the present, and finds out that person is still alive (albeit elderly) and there are still feelings between them.
• The difference has to be noted In-Universe as an unusually large age gap. The ages of the actors are immaterial. Thanks to Hollywood double standards against older actresses, many a film will cast an older male actor whose character's age is deliberately vague, meanwhile his female love interest is played by an actress young enough to be his daughter, but the gap is never brought up within the film itself. This applies to both live-action and voice acting.
• This is a Romance trope. There has to be an actual romantic relationship of at least a modest length to qualify; brief flings or one-off encounters don't qualify.
• For creatures with lifespans different from the human normal (extended or ephemeral), apply the above rules generally. If a 1,000-year-old ageless vampire is dating a 100-year-old vampire, this trope could apply, but not if they are dating a 500-year-old vampire. You might consider Mayfly–December Romance instead, where one creature has a (much) longer life expectancy than the other (but isn't always in different stages of life). For example when one partner is a normal human and the other is, for example, a Human Alien who might age much slower by our standards.

NOTE: This is an OBJECTIVE trope, meaning that it uses explicitly defined criteria; it is NOT a place to put any relationship which feels Squicky due to age differences. 30-year-olds dating 13-year-olds are not this trope.

This is Truth in Television, of course, but wasn't nearly as common in the past as some would have us think. Most couples in pre-modern days couldn't afford to marry until both the man and the woman had saved up enough to set up a household, and that could take years; it's therefore perhaps not surprising that the average ages at marriage for both men and women in Elizabethan England are identical to those in 21st century America where most of all married couples are within two to three years of each other. (It was even worse in medieval times when daughters would have to work for years to save up the customary fee owed their father's lord upon their marriage.)

Most May-December marriages in pre-19th century times were among the aristocracy, whose prominence in the history books is balanced by their small numbers (fewer than 0.5% of the population of Tudor England). Victorian-era historians, however, twisted the narrative, going as far as to destroy and deface records, to justify child marriage. At best their scholarship was unconsciously biased by their desire to justify their own cultural norms; at worst they deliberately lied.

See also Likes Older Men and Likes Older Women. Wife Husbandry is when someone intentionally raises a younger person to be their spouse. When the December is a woman, she may be Mrs. Robinson. Compare December–December Romance for romantic pairings between older characters and Merlin and Nimue for non-romantic partnerships with a large age gap and a gender difference. Often the result of an Unequal Pairing. Compare Age-Gap Algebra when a mathematical formula is proposed for determining when a romance is this (and for which the criteria listed above are one example).

noreallife

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Examples:

Anime & Manga

• The 100 Girlfriends Who Really, Really, Really, Really, Really Love You: Rentarou is a first-year in high school. Yaku, his sixteenth girlfriend, is 89 years old despite looking like an 8-year-old. It’s Less Disturbing in Context.
• "'Albegas'': Saiko Asabuki was once a student of Dr. Mizuki when she was a schoolgirl, before she graduated and became his assistant, and eventually wife.
• Ryoko Takeuchi and Daitetsu Kunikida from Blue Seed. Kunikida actually points this out in the beginning in an attempt to encourage Ryoko to date men more her own age but when she convinces him that she wants him, age difference be damned, he gives in.
• The plot (and central character) of Bunny Drop come about because of the relationship developed between the male lead's grandfather and the twenty-something Masako, who worked in his home as a helper (though whether it was romantic on her part is debatable). The grandfather is later revealed to not be the sire of Rin and was only helping Masako deal with her unsuitability towards motherhood at the time. Masako seems to harbour romantic feelings, or at least some infatuation, for the old chap though. As it turns out, the two lead characters will finally end up in this situation later on, for real.
• Several of these relationships are seen in Case Closed... and none of them end well, as more often than not one of the partners ends up dead and the other is either the murderer or one of the suspects. In an example, we have the writer Daisuke Torakura (in his 50s) and his wife Etsuko (mid-20s); he forced her to marry him via a Scarpia Ultimatum, and both she and her lover Hamura are among the suspects of his murder. (Neither of them did it.)
• In Chrono Crusade, 16-year-old Rosette is sweet on her Parental Substitute Father Remington, who publicly claims to be 27, and is actually at least 72.
• In Gravitation, 28-year-old Noriko is married to the university professor Tetsuya Ukai who looks old enough to be her grandfather. It's implied that he might not be as old as he appears, though.
• Shinra Kishitani from Durarara!! is mortified upon learning that his father's recent remarriage is to a woman younger than he is.
• In the anime Gungrave, there was Harry and Sherry. Sherry was only twelve and Harry was a full-grown man when they first met. Maria and Big Daddy is a more obvious example.
• Tatsuya Tsugawa's parents in Hekikai no AiON. His father is thirty by the time his mother is born. They later meet, and his father earns his mothers affection, and she agrees to marry him. Other than these details, little is known about them or their relationship, as they are already dead when the manga begins. They are mostly mentioned in passing by the other characters.
• Hunter × Hunter: Battera, the rich old man who has been buying every single copy of Greed Island and hiring numerous Hunters to clear the game for him, has the goal to obtain one powerful healing card from that game in exchange for a lots of money as a reward, a card that could save his lover who has been in a coma for a long time. His lover was young enough to be his granddaughter, but she was not a Gold Digger and only accepted that one modest gift that Battera made by himself. Unfortunately, she died, thus any contract he had with the Hunters are canceled and nobody ends up getting rewarded by him.
• JoJo's Bizarre Adventure: Diamond is Unbreakable: Back when she was a college student, Tomoko Higashikata had an affair with Joseph Joestar, who was already in his sixties. Sixteen years later and she's still deeply in love with him. Joseph is over two decades older than Tomoko's own father.
• Kaguya-sama: Love Is War: While she's only very briefly seen in flashbacks, Kaguya's late mother Nayotake is implied to have been in her twenties or thirties when she was born. Meanwhile, her father Gan'an was at least in his sixties at that time.
• Midori in My-HiME, who is 24 (although she tries to convince others that she's 17), is romantically interested in her professor, who is in his mid-fifties.
• Mobile Suit Crossbone Gundam has Crux Dogatie and his unnamed first wife, who died sometime before the story. His wife was in her twenties, while he was in his eighties. Though it was stated to be a political marriage, the way Dogatie tells the story implies that the relationship wasn't a bad one (indeed, Tobia suspects a case of Love Makes You Evil), and they did have at least one child together.
• Used in Pet Shop of Horrors, most prominently in a story in the Tokyo version in which a young former hostess who appears to be in her twenties marries a very frequent customer who seems to be in his fifties. This causes her stepchildren (who are all the same age as her) to despise both her and her son (who is the same age as her husband's grandchild).
• Played for Laughs in Ranma ½ when Ranma eats a Love Pill and falls for Cologne, one of the oldest characters in the series.
  Ranma: How come I never realized just how beautiful a woman in full bloom could be?!
• In Real Drive, Minamo's enthusiasm about Haru make her friends wonder whether she might be in love, even though Minamo is 15 years old and Haru is 80. The fact that Haru has been in a coma for 50 years doesn't really alleviate that. Still, things might look up for them after Haru reappears with a much younger look in the ending credits.
• In the anime adaptation of The Secret Garden, Colin's Missing Mom Lillias Craven was much younger than her husband Archibald (she looked no older than 25 while past Archibald looked almost exactly like his present and older self, save for his still not white hair), yet they still clearly adored each other. It would explain a lot about how hard he took her death.
• This is part of a chapter for Spy X Family in which Becky Blackbell comes to Anya Forger's house. Beckyr has been shown to have a crush on Loid Forger (Anya's adoptive father), and during this particular chapter she envisions a daydream in which Becky sways Loid's heart and he divorces from his wife Yor and marries Becky. She imagines the three (Anya included) moving to a luxurious castle filled with servants and chefs, and her and Loid being happily married despite the fact she's six years old and Loid is easily in his mid to late twenties. Of course as the chapter reiterates multiple times, this is all a daydream. Loid doesn't reciprocate as he fails to notice her crush at all since he treats her like she is: a child. As an added gag, Anya (who is only five) is partially supportive of Becky's crush since she would become Becky's daughter by marriage and have access to a vast array of luxuries.
• After her retirement at 20 years old, Wilma Bishop from Strike Witches married a Faraway Land commissioned officer who is 30 years older than her, surprising everyone.
• In the extras of Tsukigasa, it turns out that the significantly older Toubee had been having an affair with an 18-year-old whom he got pregnant and is now going to marry. Even his son is older than his fiancee.
• You're Under Arrest!: Ken Nakajima's Cool Old Guy father, Daimaru, is seen courting a cute Wrench Wench named Senna... and she's younger than Ken himself. Ken doesn't dislike her at all, but is rather understandably weirded out at first; by the time Senna and Daimaru actually marry, however, he has gotten over it.

Comic Books

A big problem with this trope in Comic books is the dual issue of the confusion of the character's age with the age from when the comic was first published, and the continual retcons and universe changes that are common (particularly in the last several decades) which completely re-write character histories. In particular, a large number of heroes/villains are problematic for this trope, due to extended human lifespans, but not quite long enough to qualify as Really 700 Years Old or similar. Many of their pairings are more May Fly December Romance, but due to Comic-Book Time, it's hard to categorize them. Please be careful with adding entries here.

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• In American Vampire, Jim Book's goddaughter Abilena fell in love with him. He was oblivious until she kissed him the night he faced the vampirized Skinner. He was squicked at first and refused to reciprocate. When he asks Abilena to Mercy Kill him as his vampiric urges became stronger and stronger, she agreed...but only if he gave her a child. Jim was 60 on the night they consummated their love which also happened to be his last night on Earth. Their daughter Felicia becomes one of the series' main characters.
• DC Comics:
  • Black Canary and Green Arrow managed to have it both ways. Originally, Black Canary was the native of Earth 2 (which was populated by DC's Golden Age heroes), while Green Arrow was the native of Earth 1 (which was populated by the more contemporary heroes). In other words, Black Canary was at least twenty years older than Green Arrow. This wasn't that big of a deal back in the late 1960s when the relationship was originally introduced, but as Comic-Book Time widened their age difference, Black Canary was retconned into being the original's daughter who thought she was the original Black Canary due to memory tampering (a long, very convoluted story). A few years later, Crisis on Infinite Earths retconned all of that out. In the new continuity, the Black Canary that Green Arrow dated was always the original's daughter, and Green Arrow was now at least a decade older than her.
  • The original Liberty Belle (a Golden Age heroine whose aging was slowed thanks to Applied Phlebotinum), got engaged to a man a few decades her junior. It didn't end well.
• Judge Dredd: Recurring villain P.J. Maybe (in his 30s at the time) seduced and married a 98-year-old billionaire widow by assuming her late husband's face and posing as an undercover Judge who had been sent to protect her. In spite of his psychopathy and already having gained access to her resources, he actually seemed to grow sort of fond of her.
• Alan Moore's Lost Girls features a three-way sexual relationship between Alice (in her sixties), Wendy (in her thirties) and Dorothy (in her twenties). Wendy's husband is in his fifties, but looks older.
• Turning back to Marvel Comics, Spitfire, a 1940s superheroine, had a relationship with the much younger third Union Jack on the pages of New Invaders after the blood transfusion from the original Human Torch caused her to body to de-age a few decades. The relationship didn't last, in part because of the age difference.
• Nancy and Hartigan in Sin City. He doesn't go so far as to actually sleep with her, since he thinks he's way too old (around 65 at the end of the story) to enter a relationship with a 19-year old, but they do share several very passionate kisses, and he describes her as "the love of my life" in his internal monologue. This is really a subversion, as Hartigan explicitly rejects the relationship due to the age difference (and the fact that he first met her when he saved her from the pedophilic villain of "That Yellow Bastard" when she was eleven).
• In one of the EC Comics Tales From the Crypt stories, a young man in his 20s wants to marry a woman in her mid to late 50s for her money. She turns him down since she doesn't think such a relationship is appropriate, so he goes to a witch for a love spell to force the woman to fall for him and this trope ensues.
• Viz had a one-off strip with a comic called "Bert Midler, Biddy-Fiddler" about a perverted young man with a fetish for very elderly women. He dates a 92-year-old and then, when she dies, starts looking for a new girlfriend among her similarly-aged friends at the funeral.
• There is quite a bit of it in the X-Men franchise, starting with Professor Xavier's repressed crush on Jean Grey; this was written at a time when he was supposed to be in his twenties or thirties, so it was not as extreme an age difference as it was when they reused that plot element in the 1990s for the Onslaught arc. Occasionally it verges into May-September or Mayfly–December Romance territory as characters are rejuvenated through comic book-science means or have powers that render them impervious to the effects of aging. Thus Magneto in the main timeline has the body of a man in his 30s since being de-aged and partially re-aged, which takes some of the sting out of his relationships with Cyclops' ex-girlfriend Lee Forrester and with Rogue. On a more mundane level, there was Cannonball (16 years old at the time) and rockstar Lila Cheney.

Comic Strips

• Dick Tracy: Old-time matinee idol Vitamin Flintheart (who is in his 60s more or less) and Kandikane Lane (who is about 30 at most).
• The Professor and his wife Toby in Mary Worth; they met when she was an art student. In one storyline from the mid-'90s, the Professor feared that Toby was tiring of the marriage because of the age difference.
• Only Safe Havens could play with this trope. On the one hand, Bambi/Maria, based on their age, is this trope played straight, as Bambi is in her thirties while Maria is in her sixties. On the other hand, Maria is Samantha and Dave's Kid from the Future, so in a chronological sense Bambi the older of the two since Maria's birthdate is in 2018.

Fairy Tales

• In The False Prince and the True, a young man on trial for his life is offered knowledge that will save him, for a price. He agrees, his father insists on the marriage, and she turns out to be a beautiful princess younger than he was, under a Curse.
  "You will not need to do that," answered the old woman, "you have only got to marry me, and you will soon be free."
  "Marry you?" exclaimed he, "but—but—I am not yet twenty, and you —why, you must be a hundred at least! Oh, no, it is quite impossible."

Fan Works

• Always Visible: Delia's father is somewhere in his fifties, and his wife is twenty years his junior.
• It is unclear how much of a romance we can talk about with the likes of the two of them, but in The Awakening of a Magus, Voldemort seems to believe that Malvina's heritage and brains make her a suitable potential consort, while she seems to be receptive to the idea. She also happens to be Ginny's age, and was actually set by her parents to be Draco's wife.
• The Black Prince: Harry is 56, and Eggsy is 24. While Eggsy doesn't care about the age gap, Harry does, and it ends up being one of the points of tension that leads to their breakup.
• This historical Commander Hurricane and Clover the Clever as revealed in A Brief History of Equestria. When they married, he was pushing sixty, and she was twenty-six.
• This appears to be the case in warcraft story Children of the Stars. The two leads are Night Elves, Ayuri (May) has been stated as just over 300, while Keleria (December) has lived since the War of the Ancients, which happened ten thousand years ago. Granted, they are Elves, so they both look of indeterminable age.
• The Avatar: The Last Airbender fanfic Comedy of Errors pairs up Toph (18 in this fic) and Iroh (70 as of this fic). The fic Slumber My Darling has the same pairing, but is entirely platonic, despite being a romantic relationship.
• The main plot of Dash's New Mom is about Twilight getting into a relationship with Rainbow Dash's father, who obviously is old enough to have a daughter around her age.
• Any Descendants of Darkness fic that ships Tsuzuki/Hisoka. Their physical ages (being Shinigami, their bodies don't age) are 26 and 17 respectively... but if you counted their lives as Shinigami along with their human lives, Hisoka would be in his late teens, while Tsuzuki would be nearly 100.
• Elisif the Dragon-Queen: High Queen Elisif is 23 and eventually ends up Happily Married to Madanach, who is 59.
• Empath: The Luckiest Smurf has an alternate timeline tale where Smurfette confesses her love for Papa Smurf, leading to this kind of situation that eventually has most of the entire village revolting against it.
  Tapper: I would be a fool if I didn't smurf that a 550-year-old male Smurf and an 8-year-old female Smurf do not an everlasting love smurf, Empath.
  • In the Mirror Universe story "Smurfed Behind: The Other Side Of The Mirror", its versions of Papa Smurf and Smurfette are already married...but Smurfette is not entirely faithful to Papa Smurf.
• Fate Unown is a short Pokemon fic based around the third movie. In it, Professor Oak is secretly Ash's father but Delia and Oak won't tell Ash until he's an adult. Delia and Oak are in a Secret Relationship because of their 30+ year age gap, combined with the fact Delia became pregnant when she was one of Oak's students.
• A Growing Fire In My Heart: This is one of the reasons Ember doesn't want to acknowledge that she has romantic feelings for Spike. She is 103 years old, and he is still less than 20 years old, which is still considered being a "baby dragon". Though her friends suggest she and Spike simply get engaged until he is older, Ember doesn't want to put Spike through that either. This worry is effectively eliminated when Spike undergoes a massive increase in age at the end of the story, now only being 5 years younger than Ember.
• House Divided: Optimus ends up falling for Megatron, the powerful Decepticon leader who was an active combatant in the Great War millions of years before Optimus's time.
• Harry Potter:
  • Harry/Voldemort or Harry/Tom Riddle ship. Voldemort is 53 years older. Slightly less creepy if Time Travel or the diary Horcrux is involved since then the difference would be only a few years.
  • Dumbledore/McGonagall. They both qualify as "old" now, but Word of God says she's born in 1935 while he was born in 1881. Either way, he would have already been her elderly teacher when she first passed through the doors of Hogwarts, so fanfics around when she was a student qualify (a 54-year gap).
  • In Harry Prongs Tatum, Charlus Potter's parents betrothed him to Dorea Black when he was forty-two and she was three.
• Lenore and Ragamuffin from Lenore the Cute Little Dead Girl, biologically. Lenore looks 10 years old physically and Ragamuffin looks around twenty years old in the comics. In reality they're actually 100 and 400 years old, respectively. Not-so-surprisingly, they are the Fan-Preferred Couple of the fandom.
• In Mended, Samuel was middle-aged/old when he began a relationship with the early-twenties Delia. (There's a several-decades-long age gap between them.) They're still in a relationship seventeen years later. In their case, it doubles as both an example of Teacher/Student Romance and Sleeping with the Boss as, at the time they started their romance, Delia was working as Samuel's assistant for education reasons. Samuel had wanted to come open about their relationship after Delia ended up pregnant with Ash (who is the same age as Samuel's grandson), but Delia didn't want to ruin his career with a scandal.
• Mr and Mrs Gold: As Belle and Rumpelstiltskin, she is in her early twenties while he is literally hundreds of years old. As Rose and Mr. Gold, Emma was sure that he was her father or father-in-law before she saw them kiss. Emma even once refers to Mr. Gold as a “cradle-robber.”
• Popular in Naruto:
  • Naruto with Tsunade, him being a teenager and her in her 50s, though age-defying magic makes her look 20ish.
  • Kakuzu, who is 91, is paired up with Hidan, who is 22.
• TD and Celestia eventually strike up a friendship and later romance in The Non-Bronyverse's TD the Alicorn Princess after he accidentally becomes an ageless alicorn. When they start seeing each other, TD is in his mid-twenties, and Celestia has at least 2000 years on him.
• A onesided version appears in Princess Trixie Sparkle. Astelle (who is around 16-25) falls for her elderly mentor Starswirl and mistakingly believes he loves her back. When she finds out he doesn't, she reacts badly, runs away, and comes back a Fallen Hero who curses him into becoming the Tree of Harmony.
  Trixie: You... were in love with that wrinkly old stallion?
  Astelle: I was young! I had the whole world in front of me and he was the only stallion that paid me any attention.
• Exaggerated in StarKitsProphcy. As an apprentice, both Firestar and Graystripe are attracted to Starpaw. Firestar is literally Starpaw's great-grandfather and Graystripe is his same-aged friend. Depending on how the cats age, Starpaw may not have even been an adolescent when the two fell for her. Being a Troll Fic, the narrative doesn't note the huge age gap (or the fact Firestar and Starpaw are related).
• In the Cardcaptor Sakura fic Shadow of the Dragon, Sakura's father Fujitaka ends up in a relationship with Hinami Togashi, a girl around Toya's age. After getting the blessing of Nadeshiko's spirit.
• In Vampire Lovers, Mal is a young woman, she falls in love with Fox Mulder is a 56-years old vampire agent, later both are married and sequel their expecting child named Mel.

Films — Animation

• Played with in The Book of Life. Xibalba and La Muerte are both hundreds (if not thousands) of years old, but La Muerte has the body and face of a human female in her 20s or 30s, while Xibalba resembles an old man, mostly because of his beard. Word of God reveals that Xibalba is in fact a few centuries older than La Muerte.
• Zig-Zagged in Coco. Hector and Imelda were roughly the same age in life when they got married, but in the Land of the Dead, a person looks the age they were when they died. Hector died at the age of 21, while Imelda died in her early 70s and their current appearances show that age disparity. They rekindle their romance nonetheless.
• In The Movie of the Walter Moers comic book series The Little Asshole, the titular character who is on the verge of puberty tries to get it on with the 76-year-old geezer Inge Koschmidder. That's far from the most offensive thing he does in the film.
• Played with in Wreck-It Ralph where Calhoun and Felix physically appear to be the same age, but Felix has been around for thirty years longer than Calhoun and that makes them from two different eras of video games (8-bit versus high definition).

Films — Live-Action

• About Alex sees it both subverted and Played for Laughs. The characters treat Kate and Isaac as if they have one. She is younger than him, but by at most eight years (the actors have a five year age difference).
• Absolute Power (1997): After the death of his first wife, billionaire Walter Sullivan got remarried to a much younger woman. Because of his age, he was unable to perform sexually, resulting in a bit of an open marriage while he watched. However, despite his fortune and the likelihood of her being a Gold Digger, he indicates that he genuinely did love her. Sullivan says he was drawn to Christy because, after the pain of losing his first wife, it was comforting to feel sure that his new wife would outlive him.
• Ali: Fear Eats the Soul: Emmi, a cleaning lady well into her sixties, finds love with Ali, an African immigrant no more than half her age.
• Atlantic City: Between Lou the aging two-bit gangster and his much younger, sensual neighbor Sally. When Lou is about to take a bus out of town, Sally gets the bus driver to force him off by claiming that Lou is her addle-minded father. (The film does not specify the ages of the characters but in Real Life Burt Lancaster was 67 and Susan Sarandon was 34.)
• Back to the Future Part III is a fine example, though it's never said exactly how old Doc and Clara really are. Even so, it's clear to the naked eye alone that Clara is somewhere between 30 and 40, while Doc is at least in his mid-60's or older. (The script for the original film sets his age at 65, which would make him 66 or 67 in Part III; the Telltale Games sequel puts his age at 71-72 during Part III.) It's especially telling that there's an undeniable age difference between the two, even taking into account the "full-body overhaul" Doc mentioned getting in Part II. Of course, this is putting aside the fact that since Clara comes from a century in the past, technically speaking, she would be several decades older than him.
• In The Best Offer, Virgil, an old bachelor in his 60s, falls in love for the first time with Claire (around 30). She eventually appears to reciprocate his feelings, but only as part of a premeditated plan to steal Virgil's paintings.
• Bill & Ted's Excellent Adventure has this going on with Missy, who's approximately three years older than the titular duo^note They went to the same high school; she was a senior when they were freshmen but ends up married to both their fathers over the course of the series. This is something of a sore point for Bill, who had a crush on her, but Ted is surprisingly okay with it. And at the end of the second movie, Missy ends up wedding the Big Bad De Nomolos, who's even older. Subverted in Bill & Ted Face the Music when she marries her former stepson Deacon, who is several years younger than her, though not young enough to count as this trope.
• The 1973 film Breezy has 19-year-old Breezy fall in love with the bitter 54-year-old Frank Harmon.
• Cary Grant was 59 when he made Charade, 25 years older than Audrey Hepburn. He only took the role after the writer gave all the romantically aggressive lines to Hepburn's character, so he wouldn't look like a predator.
• In Crooked House, Aristide Leonides' second wife Brenda is in her 30s, while he was in his 80s. His children regard her as the Gold Digger, while she claims she was in love with him. The slightly more objective characters, such as Sophia, at least admit that he was in love with her.
• In Deep Impact this is one of the reasons the reporter, Jenny Lerner, resents her father: In her own mother's words: "You now have a stepmother who is two years older than you". In the end, his father's wife abandons him when the comet is about to hit Earth, something she feels well deserved for him.
• Happens in Eat Drink Man Woman between Supreme Chef Chu and his neighbor Jin-Rong. Considering he's known her since his daughters were kids, that's a pretty big gap.
• First Knight Arthur is 35 years older than Guinevere, though this was likely quite common at the time the film is set. The novelisation says outright "that he was of her father's years concerned her little; she much preferred it to callow youths who spoke only of jousts and prizes"
• In Frankenstein's Castle of Freaks, Count Frankenstein has an affair with his daughter Maria's school friend Krista (who is literally young enough to be his daughter). Krista seems quite infatuated with the Count, and Maria makes a joke about the possibility of Krista becoming her mother.
• Trixie Lorraine (who's in her early 30s) and Faneul H. Peabody (who's in his 50s but looks a lot older) from Gold Diggers of 1933. These two lampshade the trope a bit in dialogue, and actually end up married after one date. (Although, given the film's title, this really isn't much of a surprise.)
• Harold and Maude sees young man Harold paired up with the aging Maude. He's 20. She's 79. In all sorts of other ways too, they are Opposites Attract.
• High Noon: Will Kane is a broken-down old sheriff who is about to retire to be with his 21-year-old bride, Amy. Actor Gary Cooper was indeed 28 years older than actress Grace Kelly.
• Holocaust 2000: After his wife is killed, the near-retirement Robert Caine (Kirk Douglas) starts a romance with a much younger Israeli woman named Sara Golan and later has a child with her. He didn't tell his adult son Angel initially because he's a bit embarrassed about the age gap, but Angel approves nonetheless.
• Holy Smoke!: Though their ages aren't given specifically, Ruth has sex with PJ, who is clearly much older. Their actors have a 36 year age gap. She declares this meant nothing, though he disagrees strongly and wants to be with her.
• In a World…: Sam Soto, the main character's father is dating a woman over thirty years his junior, making her slightly younger than his youngest daughter.
• In Quentin Tarantino's Kill Bill: Bill, an old assassin and martial arts warrior who grew up in the 1940s, is outright shown or intimated to have been in relationships with several of his decades-younger students, including the Bride, Elle Driver, and most likely Sophie as well (two of whom are blondes). Lampshaded when Bill shows up to the Bride's wedding, and she lies to the groom that he's her father.
• The Spanish movie La conjura de El Escorial (The El Escorial Conspiracy) has a very touching example with Espinosa (played by the 60+-year-old Jegen Prochnow) and Damiana (played by Blanca Jara who was 23 at the time).
• Last Vegas: Billy and his bride-to-be. He's 70 and she's 31.
• In the first Legally Blonde movie, the first case Elle works on has a twenty-something fitness guru charged with the murder of her husband, who was in his sixties. She claims she truly loved him, especially because of his... uhm, "size". She wasn't lying, and in the end, she didn't murder him. It was his daughter, who was aiming to kill her.
• In Legend of the Black Scorpion Wan was younger than the previous Emperor's own son when they married, and is undoubtedly decades younger than the new Emperor as well.
• In Leonard Part 6, Leonard's daughter dates her theater director. Leonard says he's old enough to be his father.
• Limelight has a romance between twenty-something Terry and sixty-something Calvero (played by Charlie Chaplin), though the latter refuses to admit his feelings and decides to leaves in order to let Terry pursue a healthier relationship with Neville.
• In Memoirs of a Geisha, we have Sayuri and the Chairman, who is roughly twenty-eight years older than her.
• Middle of the Night was unusual for its era (1959) in being a straight dramatic take on this trope, rather than wrapping it up in romantic comedy. Jerry, a 56-year-old man dating gorgeous 24-year-old Betty, stresses out about Betty being around younger men and worries about children, wondering if it's fair for him to father children at his age. Betty's family and friends are all against the relationship, pointing out that in ten years he'll be a straight-up old man while she's still in her thirties.
• The Milagro Beanfield War: Ladd Devine's wife is about thirty years younger than him and some of her dialogue implies that they did Marry for Love but that things haven't been as good between them lately.
• Miller's Girl: Cairo, who's 18, tries to seduce her teacher Jonathan, who's much older than her, and he is clearly into her too, though it never becomes an actual romance. Their actors were 31 years apart too.
• In The Pledge, a retired police officer in his 60s (played by Jack Nicholson) begins a relationship with a single mother (played by Robin Wright) who's his junior by about 30 years. The relationship ends disastrously when he decides to use their daughter as bait to catch an elusive child murderer.
• Prime Cut: A 50-year-old mobster (Lee Marvin) falls for a barely legal hooker (Sissy Spacek).
• While this appears to be the case in Red (2010) with between the 60-ish retired assassin Frank and the 30-something bookish Sarah, it's a little hard to tell as the actors playing them are much closer in age (55 and 46) than their characters.
• In Sin City, as noted above in Comics, this is subverted with Hartigan and Nancy. She wants it, but Hartigan ultimately rejects it due to both their age difference and the danger to Nancy it would result in.
• Something's Gotta Give: Played with. Harry is an aging lothario in his 60s who only dates women under 30. Erica, the mother of Harry's latest girlfriend, is closer to Harry's age, and is herself pursued by a young doctor in his 30s. Harry and Erica eventually fall for each other.
• Vincent and Daka show signs of this in St. Vincent (2014). Vincent was old enough to have served in Vietnam; Daka is young enough to have the ability to conceive his child.
• Surrogates: Tom Greer (Bruce Willis) and Maggie Greer (Rosamund Pike) is an interesting Subversion. Due to the surrogate technology, everyone appears as an idealized version of themselves, with Pike's character appearing late 20s or so, and Willis' as a well-kept 50-something. The relationship is portrayed as normal and not unusual. However, the reveal shows Pike's character being Older Than They Look is really in her late-40s/early 50s, an acceptable match with a late-50s Willis).
• Tales of Terror: In "The Facts in the Case of M. Valdemar", the marriage between Valdemar and Helene is a case of this, with Valdemar being much older than the wife. Nevertheless, the marriage is shown to be a happy one, with the two of them being truly in love. As Valdemar is dying, he expresses his desire that Helene finds happiness with someone else after he is gone. That thing goes hideously wrong after this is not the fault of either of them.
• Three Billboards Outside Ebbing, Missouri: Despite being in his fifties, Charlie has been dating a nineteen-year-old, which he has no problem admitting is a way to cope with his grief.
• Verfolgt (Hounded / Punish Me). A 16-year-old boy and a 50-year-old woman. She is a probation officer. He's one of her cases. It's a BDSM relationship, she's dominant and he's submissive.
• In Wild Target, the 55-year-old Victor ends up with the 27ish-year-old Rose.
• In The Young Girls of Rochefort, Solange falls in love with Andy. Just to underline the age gap, Andy's childhood friend Simon gets married to Delphine's mother. Then again Andy is played by Gene Kelly so it's understandable. Both the men are in the late 50s/early 60s, and the girls are teens.

Jokes

• A man in his 80s marries a woman in her early 20s. During the honeymoon, he asks her if her mother taught her everything that's supposed to happen then. He's grateful for the affirmative answer because he already forgot.
• A man in his 80s goes to the clinic to take the medical test for marriage.
  Doctor: You get married!? How old is the bride?
  80yr old Groom: Uhhh... she's 18.
  Doctor: Sir, do you get that any sexual activity may be lethal?
  80yr old Groom: What, you say she will die!!?
• An 80-year-old man is marrying a 30-year-old woman. His friends ask whether they have any troubles because of the age gap
  Groom: No, it's not a problem, we get along perfectly.
  Friend: It might not be a problem now, but what about 10 years later?
  Groom: I'll kick the old hag out!
• An 80-year-old man about to marry a young woman who is pregnant talks to a friend of his. The groom asks his opinion about it.
  Friend: Let me tell you a story. I have a friend who enjoys bear hunting. Every once in a while he packs his rifle and goes up to the mountains to hunt. But one day he packed an umbrella instead of his rifle by mistake, but he didn't realize until he came across the first bear: he pulled out the umbrella and pointed at it, but when he took a better look at the umbrella, he also saw the bear dropping dead right in front of him...
  Groom: That's impossible. Some other hunter must've shot the bear dead.
  Friend: And that's my opinion right there.
• A young man notices an elderly gentleman crying on a park bench, and goes to ask him what's wrong.
  Old man: I'm 80 years old, and I have a beautiful, buxom 22-year old girlfriend living with me.
  Young man: O... kay.
  Old man: She works to pay the bills, cleans the house, and cooks delicious food every day. She's great in bed, and sucks me off every night.
  Young man: Well that sounds great for you. Then what's the problem?
  Old man, bawling in tears: I've forgotten where I live.
• A somewhat disturbing take on the trope is given in a joke where an aged man who has a wife in her early 20s complains about being called a pedophile, then remarks how the accusation ruined their ten-year anniversary.

Literature

• The 1632 series gives us Sharon Nichols and Ruy Sanchez de Casador y Ortiz. Sharon is in her early to mid-twenties, while Ruy is somewhere around his mid-fifties.
• A gay example: in The Art Of Fielding, 61-year-old college president Guert Affenlight embarks on a clandestine relationship with 21-year-old student Owen Dunne, who is younger than his daughter. Not quite a Teacher/Student Romance, but close.
• Polgara and Durnik in The Belgariad/The Malloreon series, although Durnik being made a sorcerer, with the extended lifespan that comes with it keeps it from being a Mayfly–December Romance.
• On the horizon in Bleak House, in which Mr. Jarndyce proposes to Esther; the trope is ultimately averted when Jarndyce realizes that Esther loves Allan Woodcourt.
• The Canterbury Tales: The wife's name is actually May, while the husband's is January. Chaucer explicitly says it's a bad idea, though, and this type of pairing is frequently satirized in medieval literature (in particular, the jealous old husband with a hot young wife is a common butt of jokes, in Chaucer and elsewhere).
• Chocoholic Mysteries: Joe Woodyard's first wife, Clementine Ripley, was fifteen years older than him. The trope name is even mentioned in a tabloid headline ("TOP WOMAN DEFENSE ATTORNEY MARRIES TOYBOY LOVER IN MAY-DECEMBER ROMANCE") in Bear Burglary.
• Possibly Amara and Bernard in Codex Alera, with Amara being in her late teens and Bernard being old enough to have adult children (from his late wife), and thus likely at least pushing 50. In and of itself the relationship is not that uncommon, considering the Aleran culture is a conservative society based on ancient Roman civilization, and the romance between them works mostly because Amara is presented as a consenting adult who is also a very capable and professional spy for the Crown.
• In A Damsel in Distress, the lord ends up marrying a chorus girl when he has children old enough to marry themselves. She appears to be about their age.
• Dr. Strong and his much, much younger wife Anne in Charles Dickens' David Copperfield.
• Discworld:
  • Played with in Lords and Ladies. Nanny Ogg is somewhat disturbed by the attentions of the apparently much younger dwarf Casanunda, until he points out that by dwarf standards her age makes her barely a teenager.
  • Played straight with Cohen the Barbarian and Bethan in The Light Fantastic. She refers to "eight years" of maintaining her Virgin Power, which probably puts her in her twenties; he reflects that "If I wash twenty yearsh younger, I'd be shixty-sheven". When Rincewind meets Cohen's daughter in Sourcery, he pegs her and Bethan (whom Cohen has married at this point) at about the same age.
• Don Quixote: Deconstructed with Altisidora in the second part: Altisidora, a 14-year-old maiden at the Duke's palace, pretends to be in love with Don Quixote, a 50-year-old man. He stoically supports her teasing and mean pranks because he believes she's in love with him because he is a knight, but he never attempts anything because he wants to be loyal to his (imaginary) lover Dulcinea and is very happy when he abandons her and the palace. Being an honest man, he confesses to Sancho that Altisidora's feelings caused him more confusion than pity.
• Time Enough for Love: Lazarus, an immortal, married his adopted daughter Dora Brandon whom he has raised since childhood, and is quite distraught when she dies after "only" 70 or 80-odd years, and remains celibate for 100 years after that before he finally decides to get on with living.
• The Dresden Files:
  • Small Favor: When Harry Dresden, who at this point is in his early thirties, begins a relationship with Anastasia Luccio, who grew up during Victorian times. One book later in Turn Coat Harry mentions that they have "wild monkey sex". They both expect to potentially live centuries, however.
  • Explicitly mentioned as a problem for many wizards in the series, since their very-much-extended lifespan puts most relationships with normal humans into May Fly December Romance status.
• The Elenium ends with the 18-year-old Queen Ehlana married to her fiftysomething-year-old knight-protector Sparhawk. Genuine love match on both sides. And then Sparhawk's boyhood friend (late '50s) marries the maid (18).
• Julius Caesar gets together with Servilia, mother of his adopted brother Marcus Brutus, in Conn Iggulden's Emperor books. In these books, Caesar and Brutus are the same age.
• V. C. Andrews has several examples in her novels, but probably the most notable one is in Garden of Shadows, where Garland Foxworth (in his 70s) married 16-year-old Alicia, who was genuinely in love with him and was more than a decade younger than his son Malcolm.
• Gilead: Rev. Ames was in his late 60s when he married Lila, less than half his age, who soon bore him a son. In the time frame of the story, not quite a decade has passed and a 76-year-old Ames is growing concerned about handsome young Jack Boughton hanging around his wife.
• In Girl Overboard by Justina Chen Headley, the main character Syrah's parents are far apart in age; her mother is in her 40s and her dad is 70.
• In The Good Earth, by the end of the novel, Wang Lung, now an old man, takes Pear Blossom, a young girl, as a concubine. Pear says that she prefers the quiet devotion of older men to the fiery passions of the young.
• Her Father's Daughter: Inverted. Donald's mother informs him that there is no chance that he can marry Linda because he's only a year her elder, and he's going to college.
  "By the time you are ready to marry and settle down in life, Linda in all probability will be married and be the mother of two or three babies."
• The Honor Harrington novels have a somewhat complicated case (thanks to the presence of the longevity-boosting prolong treatment): Hamish Alexander is 39 years older than Honor, looks like he's about fifteen years older and it doesn't make much of a difference anyway because both still have the vast majority of their expected lifespan left to them (prolong recipients can live 200-300 years). There are also occasional tragic examples involving relationships where only one participant has received prolong. These can turn the trope on its head since the prolong recipient can be far older while still looking a lot younger than their partner.
• Coleman Silk and his mistress Faunia Farley, the protagonists of The Human Stain, by Philip Roth. Coleman is in his seventies and Faunia in her thirties, for which Coleman catches a lot of flak.
• The Immortals After Dark series by Kresley Cole features this fairly often, with an extreme case being the relationship between Lothaire, about three millennia-old, and Elizabeth, who's in her early twenties. The women sometimes play the December part, funnily enough, but only the three Valkyrie sisters Myst, Kaderin, and Daniela, who are about two thousand, to Nikolai, Sebastian, and Murdoch, three brothers who are about three hundred. So even in those cases, the guys aren't exactly babies by immortal standards.
• In Let Me Call You Sweetheart, Suzanne had a long-term affair with Jonathan Hoover; she was in her mid-twenties while he was in his early fifties at the time, making for a gap of around three decades. It's deconstructed as they weren't truly in love with each other, despite Jonathan treating it quite seriously – he was and still is in love with his wife but struggled to cope with her declining health, while Suzanne made him feel young and desirable again. When his wife found out about the affair, Jonathan felt foolish and decided to end it. It then turned out that Suzanne just seemed to like the attention he showered upon her and had already moved on to other lovers, much to Jonathan's displeasure.
• British statesman Lord Chesterfield retells a Real Life example in Letters to His Son: "If my brother had had some of those self-conversations, which I recommend, he would not, I believe, at past sixty, with a crazy, battered constitution, and deaf into the bargain, have married a young girl, just turned of twenty, full of health, and consequently of desires." (letter 260)
• In Devon Monk's Magic to the Bone, Allie is shocked to see that her last stepmother is at most a year older than she is. Violet admits that she would be shocked, too, if her father married someone her age, but assures her it was a love match.
• Wilkie Collins' Man and Wife has three, though in the first two cases we only meet the wife after she's been widowed.
  • Sir Thomas Lundie would have been 30-40 years older than his second wife (at the start of the action, she's in her mid-thirties; Sir Patrick, Sir Thomas' younger brother, is 70).
  • Mrs. Glenarm is 24, and her late husband is stated to have been old enough to be her grandfather.
  • The novel concludes with the marriage of Anne Silvester and Sir Patrick Lundie, although Sir Patrick is decades older.
• The Mary Russell mysteries by Laurie R. King feature a young woman who marries Sherlock Holmes. According to the book where they actually married, he was fifty-nine to her twenty-one when they married.
• In Oliver Twist, it's implied by Mr. Brownlow that Oliver and Monks' father Edwin Leeford and his unnamed first wife aka Monks' mother were like this. Uncommonly, she was the older one. And theirs was a very unhappy union.
• Reena's father's second marriage from The Poison Apples. He's in his fifties and his second wife is in her twenties.
• Reaper (2016): Hawk (or Michael) is four hundred to Jex's eighteen, although as people's development ceases when they join Game he insists that the centuries between them don't count. Due to the ways society has changed since he went into Game, he says she's much more of an adult than he is.
• Repeat It Today With Tears by Anne Peile details the romance between 16-year-old Susie and her long-lost father, who is in his mid to late 50s. She lies about her age and pretends to be 19, but he still frequently comments on the age difference between them.
• Referenced by Miranda in The Riftwar Cycle: she makes comments about being in a relationship with a "youngster" like Pug. (He's in his 90s, she's upwards of 300 years old, nobody knows how long either of them is going to live.)
• In The Rogue King, Koral is thrice Lasil's age and, presumably, has only ten more years to live.
• While strictly speaking a Mayfly–December Romance, the feeling of this trope is impossible to avoid in The Sharing Knife books by Lois McMaster Bujold, especially when 18-year-old Fawn Bluefield takes 55-year-old Dag Redwing home to her 53-year old father... and insists on marrying him. For those counting, that's a 37 year age gap, though Dag looks like he's in his late thirties rather than his true age. The fact that they both expect to last 50 to 60 more years and, barring violence or illness, die of old age about the same time^note Dag's grandfather died of old age at 126 years old. is of little comfort to those around them even without the Fantastic Racism in the mix. However, their relationship is one of mutual love, trust, and respect, so the potential for Squick for the readers is dialed down quite a bit.
• In Sid Stills' Blues (Three-Quarters in the Bag in Alphabet City), sixty-one-year-old Sid enters into a romantic relationship with Nathan, who is twenty-five.
• A Song of Ice and Fire:
  • Walder Frey's current wife, Joyeuse Erenford, is 64 years his junior, and married him when she was 16 and he was 90.
  • There is a forty-year gap between Jon Arryn and Lysa Tully, and they married when she was sixteen years old and he was around sixty. The betrothal was political, because Jon desperately needed an heir, while Lysa was previously impregnated out of wedlock, and Defiled Forever in the eyes of many. Lysa's sister, Catelyn, understands how unfair it must have been to Lysa to be married off to a man much older than she is, when Cat's own arranged (but perfectly) husband, Ned Stark, is only a year older than her.
  • Shae, Tyrion Lannister's prostitute mistress, eventually abandons him in favor of his father, Tywin. She is barely out of her teenage years, while he is nearly sixty.
  • Elaena Targaryen and Alyn Velaryon. When their relationship started, she was in her early twenties, while he was in his late fifties and had an adult daughter who is sixteen years older than Elaena.
• In Gene Stratton-Porter's The Song of the Cardinal, the main character's parents are described as "a tough old widower of many experiences and variable temper" and "a fine, plump young female."
• The Star Trek Expanded Universe marries Spock off to the much younger Saavik, who, even though Vulcans have substantially longer-than-human lifespans, qualifies as Saavik is human-equivalent late 20s, and Spock is pushing 60-equivalent.
• In the seventh Tales of the City book, Michael Tolliver Lives, Michael starts a relationship with Ben, who's more than twenty years younger. The May-Decemberness is compounded by the fact that Michael contracted HIV in the eighties, and many of his friends died of AIDS; Michael still has a lingering sense of his own mortality relative to Ben, who came of age after treatment for HIV changed it into a survivable chronic condition.
• Tearmoon Empire: Ruby Etoile Redmoon, whose age is close to Princess Mia and the daughter of the Redmoon duke, is in love with Vanos. the vice captain of Dion who is old enough to be called an uncle.
• Agatha Christie's Three Act Tragedy hints at a budding romance between the 55-year-old Charles Cartwright and the 25-year-old Egg. This is subverted when Charles turns out to be the Serial Killer, and Poirot suggests that Egg would be happier with Oliver Manders, who is closer to her age.
• In the Colleen McCullough novel Tim, the mentally disabled title character and the woman who has employed him as a gardener fall in love, despite the fact that she's at least twenty years his senior.
• In the Warrior Cats prequel Bluestar's Prophecy, Pinestar and Leopardfoot have kits sometime after Leopardfoot becomes a warrior. Pinestar was already a leader on or close to his last life when she was born.
• In Robert Jordan's The Wheel of Time series, Aes Sedai (especially of the Green Ajah) are known to have relationships with their warders, despite being hundreds of years older. On the other hand, this is made a little less unusual by the fact that Aes Sedai tend to appear much younger than they are. And, of course, the fact that everyone lives a very long time.
• In Wild Swans, 25-year-old Yang Yu-fang marries Dr. Xia despite a forty-year age gap and the vociferous protests of his family.

Live-Action TV

• All in the Family: A Season 9 episode of "Family" saw Archie's brother, Fred (who is in his mid-50s), marry an 18-year-old girl.
• All My Children: A good chunk of Adam Chandler's marriages — Dixie, Gloria, Liza, Annie — were examples of this.
• Amen: Deacon Ernest J. Frye was much older than many of his love interests, especially a young environmental lobbyist played by Halle Berry (28 years his junior), prompting his daughter Thelma to exclaim, "No wonder he's acting like a teenager. He's dating one!"
• On the soap opera Another World, Rachel Davis (late 20s) met and fell in love with Mac Cory (early-mid 50s). They were married three times each until Mac's death in 1989. Mac was even around the same age as Rachel's mother Ada Hobson.
• Arrested Development has Buster with Lucille Austero, then later GOB with Lucille Austero. They're both 30+ years younger than Lucille, and though both are pushing 40.
• Babylon 5 has Londo Mollari, an aging politician, in a brief but passionate romance with Adira Tyree, a beautiful dancer a few decades his junior. Despite the age difference and the hyper-sexual nature of the relationship, the show makes it clear that she is truly the love of his life.
• Baywatch: Twenty-something Aussie lifeguard Logan Fowler dumps Caroline Holden for 60-year-old widow Kathleen Huntington, and marries her to get his green card.
• HBO's Big Love gives us the Juniper Creek couple which is an Exaggerated Trope: Rhonda Vulmer and Roman Grant. Rhonda is fifteen while Roman his in his seventies. There are plenty of other examples discussed in-Series where grandfather-aged men take teenagers as wives.
• In Charite, 17-year-old actress Hedwig Freiberg intially only seems to be interested in Professor Robert Koch, 30 years her senior, because he's a prestigious Meal Ticket. But when she also stands up against his wife to get him help when he's ill, has his back during the scandal that destroys most of his career, and marries him after his fame has paled somewhat, it becomes increasingly clear that she really loves him.
• An episode of the The Cosby Show had a 53-year-old colleague of Cliff's introducing him and Clair to his new girlfriend, who's in her early-to-mid twenties. Although initially shocked at the age difference, the two were relieved to see the young woman was not an airhead and that the couple appeared to be genuinely happy together.
• Deb and Lundy on Dexter. Deb's age is somewhat unclear because Dexter is supposed to be only slightly older and he's in his late thirties, which would make Deb in her mid-to-late thirties, but she's treated as if she was in her twenties^note which is the real-life age of her actress. In season 2, she starts an Office Romance with a much older Agent Lundy (in his sixties) who could easily be her father.
• BBC soap opera Eldorado opened with a 50-something main character having recently married a 17-year-old girl. Public controversy over this storyline was later cited as a possible reason for the show's failure.
• Flowers (2016): Hylda, Amy's girlfriend at the start of series 2, is quite an aged priest, though she's supposedly pretty badass, too. The actresses age gap was thirty three years.
• Forever: The 22-year-old victim in "Look Before you Leap" was dating her 57-year-old professor. He tried to break it off because he felt she deserved someone her own age and wanted her to be happy.
• In Gilmore Girls, Paris dates her much older professor when she is a freshman at Yale. She names this trope word by word when she confesses their Secret Relationship to her roommate Rory. Rory is quite squicked by it and says it's more like May and Ming Dynasty Romance. Rory's mom Loralai keeps guessing his age and the final "in his sixties" also feels unsettling to her.
• Happens a couple of times on The Golden Girls:
  • In one episode, Blanche is excited to date a man in his early 20s, and Rose's visiting mother relates that she too once had a romance with a younger man after Rose's father died. But as Blanche spends more time with him, it becomes clear that he wants her to be a mother figure, which is not what she signed up for.
  • Dorothy's son Michael announces that he's engaged, but warns Dorothy that his fiancee Lorraine is black, which she is okay with. But when he brings her to visit, it turns out he didn't mention that she is over twice his age, to which Dorothy strongly objects. Ironically, Lorraine's own mother has the opposite reaction: Lorraine said her fiance was younger, not that he was white. It took the couple announcing that they're also pregnant (hence the sudden engagement in the first place) for the mothers to stop bickering and get on board with the marriage.
• The third season finale of Inspector Morse indicates that one of these is starting to develop between the title character (implied to be in his late 50s) and pathologist Grayling Russell (apparently in her late 20s or early 30s). She falls victim to Chuck Cunningham Syndrome before the fourth season, however, so we never find out whether or not it actually went anywhere.
• Invoked by name by Cuddy in an episode of House, when the patient is a middle-aged man dating a woman in her 20s. House retorts that it's "May-October at worst".
• Little Britain had a recurring sketch in series one about a teenage boy (Jason) falling in love with his friend's elderly grandmother ("Nan".) A deleted scene from series two showed that they had finally got together and begun a sexual relationship.
• British Sitcom May to December has a late-middle-aged man marrying a woman about the age of his children by his late first wife. In the first season/series of the program[me], the older Scottish lawyer/widower is 53 and his younger P.E. teacher girlfriend is 26. He's her divorce lawyer and they fall in love, and much is made about this, from speculation about whether she's in it for the money or whether he's just a doddering old fool robbing from the cradle.
• Million Yen Women: Twenty-four-year-old Yuki turns out to be married to an old man. This gets pointed out by her husband in the flash-back that has him propose to her when she's twenty-one.
• Modern Family: Jay is over 60, Gloria is in her 30s.
• The Night Manager: Roper is far older than Jed. Hugh Laurie as Roper is thirty one years older than Elizabeth Debicki, who plays Jed. Laurie was about fifty six at the time, and she around twenty five.
• Shelly and Holling in Northern Exposure. He's about forty years older than her. However, he's often afraid of outliving her because nearly all of his male ancestors have outlived their wives by forty years or so, and are somewhat known for their longevity.
• Ozark: Wyatt, in his early 20s, gets into a relationship with Darlene, apparently in her 60s. Several people, including Darlene, state that she's old enough to be his grandmother.
• Quantum Leap has Al and his girlfriend Tina. The one time she is shown she appears to be in her twenties or thirties, whereas Al is in his sixties.
• One of these is the center of a big plot point in Chilean Soap Opera Romane. The father of the female lead Jovanka (Melquiades, leader of the local Roma group, a Foxy Grandpa in his late 50s/early 60s) marries a girl in her late teens (Milenka, who's younger even than Jovanka's daughters aka Melquiades' own granddaughters). In a subversion, it begins as a Perfectly Arranged Marriage since Milenka herself does like Melquiades as a person. Predictably, however, the drama started to come out, and soon things went downhill.
• Rome:
  • Caesar is more than thirty years Cleopatra's senior.
  • Then there's Caesar's daughter married to Pompey, apparently rather happily. Caesar was younger than his son-in-law.
  • Posca seems to be in his fifties while Jocasta is probably in her twenties.
  • Then there's Octavia, who is almost paired with Pompey in the first episodes, then married off to Antony (who is actually her mother's boyfriend) and also has a love affair with Servilia, who is in her fifties.
• Parodied in the Saturday Night Live skit "Meet Your Second Wife", in which three male contestants are introduced to the girls who will become their second wife. Despite the fact that this won't happen until well into the future, all three are very distressed at the age of the girls—13, 5, and a three-month old fetus.
• Seinfeld: In one episode, Elaine dates a man who is 66. Though she gets teased over it a bit, Elaine seems to be happy with this. However, he then has a stroke and nearly dies, convincing her to break up with him. The way she does this though is to suddenly spring it just as she's been feeding him.
• Lampshaded in True Blood. When Sam declares his love for Nicole (because he could sense that she was pregnant), her mother objects because Nicole is only 22. Then she turns to Sam and says, "And may I ask how old you are, silver fox?" He...doesn't answer. Nonetheless, she grudgingly comes to accept their relationship in future episodes, though "Silver Fox" remains her nickname for him.
• The Twilight Zone (1959) episode "A Short Drink from a Certain Fountain," deals with the December part of a romance attempting to reverse the clock. It goes as well as one can expect.
• In Un gars, une fille, Guy's dad, a sixty-something career womanizer, ends up settling down with Mélanie, a twenty-something stripper. They even end up having a child together.
• The Umbrella Academy has Hazel, in his 30s, form a relationship with Agnes, in her 60s. They escape the apocalypse together and spend another 20 good years with each other in a different timeline.
• The Undoing: Jonathan has an affair with Elena, a woman young enough she could be his daughter (his actor Hugh Grant is thirty five years older than actress Matilda De Angelis portraying Elena), even fathering a baby with her. She possibly Likes Older Men, but it may be that he (initially) just treated Elena much nicer than her husband, who she fights with constantly.
• Victoria: The first half of Series 1 focuses on an impossible (and by necessity platonic) romance between Lord Melbourne (who was in his mid-50s, and here played by an actor in his late 40s) and 18/19-year old Queen Victoria. The romance is impossible partly for the age difference, but also for reasons of class,^note It would not do in those days for a monarch to be with someone of as low a rank as a non-sovereign viscount politics,^note Too strong an association with a Whig leader would suggest partisanship on the Queen's part. While this would not have been problematic a few decades earlier, the norms of the 1830s and 40s were such that the monarch had to be seen as neutral. and Melbourne's marital history.^note Lord M's late wife, Lady Caroline Lamb, was notorious as the mistress of Lord Byron—even after calling Byron "mad, bad, and dangerous to know". Association of the monarch with such a house would not do even if Lord Melboune were otherwise eligible. Although critics cried that this isn't Truth in Television, there are many biographies of Victoria and Lord M that support the belief (which also existed at the time) that their relationship was a romance of sorts; certainly, Victoria had a stronger emotional bond with Lord M than with any of her later Prime Ministers, even the ones she liked (e.g. Disraeli).
• Why Women Kill:
  • Tommy Harte is a product of such a marriage between his My Beloved Smother Naomi (who is hinted to be a Gold Digger) and his older father Edmund (who died at 57 prior to the series, likely when Tommy was younger); there was a family photo of a grade-school aged Tommy with the youthful and blonde Naomi with a graying and older man. Averted somewhat when the elder Harte revealed in a post mortem voiceover that his marriage with Naomi wasn't a happy one.
  • Tommy himself starts dating Simone, one of his mother's friends, after having had a massive crush on her since the moment he saw her as a child. Despite the relationship having lots of ups and downs (not all of which have to do with the fact that he's eighteen and she's in her forties), he's shown to be sincerely in love with Simone, and she grows to care for him very deeply. They ultimately break up when Simone's husband Karl contracts HIV, which quickly turns to AIDS. While the realization that Karl was gay, using her as The Beard and lying about it for a decade, and routinely cheated on her is what drove Simone into Tommy's arms to begin with, she and Karl are still the best of friends, so when he's very, very sick and clearly doesn't have much time left, she unhesitatingly decides to remain at his side, which upsets Tommy. When they break up, Simone sadly admits that they're just too far apart in age and life experience for it to really work long-term. In the "Where Are They Now?" Epilogue, it's revealed Tommy became a famous painter and Simone owns one of his works, implying they're on good terms.
• On Yellowstone Loyd is an aging cowboy in his late fifties. He starts dating Hassie, a 25 year old rodeo barrel rider. Hassie is the one who initiated the relationship when she picked Loyd out of a room full of younger cowboys and asked him to dance with her. Loyd is very happy with her but acknowledges that it is ridiculous how he is twice her age and acting like a teenager in love.
• Young Sheldon: June and Justin in "Crappy Frozen Ice Cream and an Organ Grinder's Monkey". Indeed June is old enough to be Justin's mother.

Music

• The old Kurt Weill-Maxwell Anderson standard "September Song" is sung from the viewpoint of the "December" half of one of these. In its original context, in the musical Knickerbocker Holiday (which also has a song "May And January"), it's also something of a Villain Love Song.
• This is the underlined theme of the famous song "Caballo Viejo" ("Bamboléo" for the ones who only had heard the Gipsy Kings version). The song is from the perspective of an old man who suddenly finds he has fallen in love and decides to go in quickly because, as an "old horse", he thinks he won't have enough time to enjoy this romance.
• Chihiro Yonekura's Ten years after, the ending of Mobile Suit Gundam The 8th Platoon. Its lyrics talk about a young girl crushing on an older man and hoping she can hook up with him in 10 years.
• Pet Shop Boys, "Young Offender". An older man is in a relationship with a younger man, and looks on bemusedly as the younger plays computer games and pouts like an angsty teenager. The narrator sings, "I've been a teenager since before you were born!"
• The Garth Brooks
  • Song "That Summer" concerns a romance between a "teenage kid" and a "lonely widowed woman." For bonus points, he can't stop thinking about her, even years later when he's with someone else.
  • "Digging For Gold" from In The Life Of Chris Gaines is a marriage of a millionaire and a wife who is young enough to be his daughter that quickly turns sour when the wife shows she's only in it for the money.
• "Maggie May" by Rod Stewart. She's the "December" half. And the narrator is well aware that she's nothing more than a jerk to him, but he's too in love to leave her. The song is based on Real Life events. Rod Stewart was seduced by an older woman when he was in his teens, and he describes it as a traumatic event.
• "Birthday" by The Sugarcubes, aka Sykurmolarnir, details the love affair between a five-year-old and a fifty-year-old.
• "Our Ages or Our Hearts" by Roberta Flack is about a woman in a relationship with someone much older (or younger) than her. This age gap is large enough to be deemed inappropriate by society, but the woman doesn't care. She asks her lover if they will stay with her or leave her due to judgment from others and the pressure of societal norms.
• "Goin' Blind" by KISS from Hotter Than Hell details a doomed romance between a 93-year-old and an underage girl.
• While by definition "Es war Sommer" by Peter Maffay (he was 16, she 31) does not count, German comedian Otto Waalkes made a parody of the song that reduced any potential ^note "Officially", they go to the strand and hold hands until sundown. Unfortunate Implications by increasing his age to 18. Oh, and hers to 88.
• "Too Old To Fall In Love" by The Poor Relations is about a older man thinking he's too old for his lover.
  "So think of your future
  The summers are few
  When you turn 40, I'll be 72."

Myths & Religion

• In the Book of Genesis, Abraham's beloved first wife Sarah dies of old age. (Apparently, she would have lived as long as Abraham himself if she hadn't questioned God earlier in the narrative.) Sometime after her funeral, he marries another woman by the name of Keturah, who bears him seven sons. Some scholars believe that Keturah might have been Abraham's concubine Hagar (who had borne his first son, Ishmael) going by an alias, others think she's a completely different person.
• Apparently, King David's ancestors Ruth and Boaz were another of these match-ups. In fact, when Ruth says that Boaz should marry her according to the local laws, his immediate response goes by the lines of "well, no matter what the law says, I'm an old man already so you shouldn't seek me out..."
• In several Christian denominations, it is believed that Joseph was already an old man, previously married, and had sons and daughters (St. James, brother of Jesus, and St. Jude^note Not to be confused with Judas among them) when he married Mary, who was in her early teens (according to one of the Gnostic gospels, she was sought to be married off by the priests raising her since she was coming into womanhood and they feared she would defile the Temple "after the manner of women").
• The Book of Mormon: It's not clear exactly how old Coriantum was when he married "a young maid", but his late wife was 102, and he himself was said to be "exceedingly old," eventually dying at 142. The remarriage did, however, succeed in producing heirs. (How they felt about each other isn't stated, but given that he was apparently monogamous, despite the fertility problems, in a society where multiple marriages were normal, he probably didn't marry on a whim.)

Professional Wrestling

• Dawn Marie was involved in a Kayfabe romance between her and Al Wilson (father of Torrie Wilson and who is a whopping 29 years older than her). Mr. Wilson would later pop the question to Dawn Marie, and would later marry her in the ring without incident. It ends tragically however, with Al Wilson having a heart attack during their tiring honeymoon.

Radio

• Our Miss Brooks: Miss Brooks is the subject of two unwanted aged geriatric suitors. In "The Telegram", she's the object of affection for Mrs. Davis' nonegenarian Uncle Corky. Meanwhile, the younger, but still senior citizen, Mr. Barlow falls for Miss Brooks in "Puppy Love and Mr. Barlow".

Theatre

• In City of Angels, Alaura's age is unstated, but she's obviously a Femme Fatale in the prime of her life. Her fabulously wealthy husband, Luther Kingsley, is 75 years old and not doing too well in an iron lung; not surprisingly, she's scheming to hasten his demise.
• Deconstructed hilariously in Donizetti's opera buffa Don Pasquale. In it, an old bachelor named Don Pasquale feels the urge to get married at the expense of his nephew Ernesto. To get back at the old blowhard, Ernesto and Norina, a young widow who is Ernesto's girlfriend, put Pasquale through a simulated marriage with a little lady named "Soforina" (Norina in disguise). But once Pasquale gets "married", "Soforina" quickly puts him through the Awful Wedded Life. By the time the ruse is revealed, Pasquale learns that he's just not cut out for marriage, and he blesses Ernesto and Norina's marriage.
• In Goethe's Faust: First Part of the Tragedy, Faust, an old man, has a disastrous relationship with Marguerite, who is in her late teens. However, due to a rejuvenating potion, Faust has the appearance of a young man, and Marguerite never learns his true age.
• H.M.S. Pinafore:
  • Captain Corcoran marries Buttercup, his nurse when he was a baby.
  • Ralph Rackstraw is Corcoran's age and Corcoran is Josephine's father, Ralph is marrying a woman young enough to be his daughter.
• Niccolo Machiavelli's Mandragola features the "hot young wife openly cheating on dumb older husband" variant.
• Teased upon but ultimately Defied in Die Meistersinger von Nürnberg by Richard Wagner. Young Eva Pogner has known her aged neigbor Hans Sachs all her life and admires and respects him deeply, so when a singing contest is approaching with Eva's hand as the promised reward, Eva tells Hans she won't mind if he, a widower, wins it, and even invokes She's All Grown Up. However, Hans tells her that he is far too old for her and that it would be like having "a child and a wife" at the same time. In the final act, when she sees him helping Walter, the young man she loves, prepare for the contest, Eva is so overwhelmed that she cries that she would have chosen Hans, and Hans implies he might have tried wooing her, but he knows well the story of Tristan and Isolde and how it ended for King Mark, so thanks but no, thanks. Eva marries Walter with Hans's support and blessing.
• A much, much older lady trying to make sure her twentyish charge doesn't go for someone remotely his own age is a plot point in The Mikado.
• In The Most Happy Fella, Tony Esposito, in his late 50's, marries Rosabella over his sister's objections that he's too much older than her. He acknowledges that he's old enough to be her father.
• Pokémon Live! contains some Ship Tease between Ash's twenty-something-year-old mother Delia and Professor Oak. When Delia goes out with Oak, Ash coyly tells the professor not to bring his mom back too late.
• South Pacific: Emile de Becque is a middle-aged owner of a plantation in the South Pacific who falls in love with a young World War II nurse stationed there, Nellie Forbush. Their mutual Establishing Character Moment is a duet in which he expresses fear that he is too old for her, and she expresses the same fear that she is too immature for him. When Emile proposes, he makes a point to remind Nellie that if they have children, he won't live to see them grow up.

Video Games

• Assassin's Creed Origins depicts the relationship between Julius Caesar and Cleopatra with historical accuracy in regards to their ages: when the two first meet, he is in his mid-50s, while she is 21.
• Interestingly, young Muslim rulers (always male) in Crusader Kings II can reap considerable benefits by having such relationships. By having 1 or 2 wives (out of 4) in the "December" age group, "May" Muslim rulers can reduce the number of sons they have, which help with issues of succession and rivalries come the next generation.
• One of the potential romance options in Cyberpunk 2077 is Kerry Eurodyne, who is about 70-80, while the Player Character V is canonically 27. This is a universe with advanced rejuvenation treatments and aesthetic implants, so Kerry looks to be in his mid-to-late thirties, except for his grey hair.
• In The Elder Scrolls backstory, Emperor Tiber Septim, the founder of the Third Tamriellic Empire, would engage in one of these with the young Dunmeri noble Barenziah. Septim was Barenziah's senior by many decades when their relationship began. Barenziah was being groomed to be Septim's loyal Puppet Queen in her newly vassalized homeland of Morrowind. Barenziah actually became pregnant by Septim, and since a bastard child with a Dunmer mistress would be very inconvenient for Septim, he ordered that the child be magically aborted, much to Barenziah's dismay. Ironically, it is also a Mayfly–December Romance in the opposite direction, as Barenziah is a Long-Lived Dunmer who would go on to outlive Septim by centuries.
• Fire Emblem has MANY cases.
  • Fire Emblem: Thracia 776: Princess Miranda's ending says that she fell in love with a "certain knight" and they got Happily Married. There's only one knight that fits such a description: Cool Old Guy Connomool, who worked for Miranda's Disappeared Dad and then swore loyalty to her.
  • Fire Emblem: The Blazing Blade: A definitive case in regards to Isadora (mid-20s) and Renault (at least in his 50's, though he looks fine for his age.)
  • Fire Emblem Fates: A Female Avatar (looks are customizable, but she's probably no older than late teens) can strike one with her retainer and Parental Substitute Gunter (age isn't fully clarified, but going by his Silver Fox looks, he's very clearly in his 50's), the Hoshidan strategist Yukimura (a pupil of the Avatar's Disappeared Dad, is in either his late 30s/very early 40s), World's Strongest Man Fuga (mid-to-late-40s, already the Parental Substitute of a boy in his mid-teens who is also a marriage candidate for the Female Avatar, often mentions how old he is compared to others) or the Kohga rogue Shura (at least in his mid-late 30s since he was almost surely a teenager when he helped abduct Azura).
  • Fire Emblem: Three Houses: Professor Hanneman starts the game already in his 50s, and he doesn't disimulates it. Despite that, his potential romance partners include Byleth (26), Edelgard (24) and Dorothea (25), about the only option this doesn't applies this is Manuela, who ends the game at 40 years old.
• Defied by Roland in Fleuret Blanc. He would be the May to Judge Aunty's December... if he didn't consider her an Abhorrent Admirer precisely because of the age difference.
• The main premise of Hidden City's "Crime at the Wedding" case is the marriage between the 70 year old Abner Old and the 19 year old Mirel that gets disrupted by a possible assassin seeking to take the groom's life.
• The Legend of Zelda: Breath of the Wild has Robbie and Jerrin. The former is a Long-Lived Sheikah (a tribe of humans capable of reaching 150 under normal circumstances) who is at least 120 when Link meets him in the present day, while his wife is a Hylian who is about 50 years younger than him. They're Happily Married and have a mixed-race son named Granté.
• Colonel Volgin and Major Raikov in Metal Gear Solid 3: Snake Eater. Volgin's old enough to have fought in World War II (the story takes place in the sixties) and Raikov seems to be in his twenties. Given the sort of person Volgin is, this may be one of the least potentially squicky things about their relationship (although there are slash fans who like that sort of thing).
• There are trainers in Pokémon Battle Revolution with the trainer title 'May-December Couple'. And yes, you do get to battle against them. The "Mays" are all cute girls while the "Decembers" are huge, burly guys.
  • Pokémon officially gets one in the Isle of Armor DLC for Pokémon Sword and Shield, which introduces a dojo with an Old Master named Mustard and his wife Honey. Mustard looks the part, with wrinkles, gray hair, and a noticeable slouch, but his wife looks like she's could be in her mid-20s or early 30s.
• Transistor: The game heavily implies that, among The Camerata, Asher and Grant are married. Their official ages puts them almost 30 years apart in age, with Asher being a writer in his late 20s while Grant, the Administrator of Cloudbank, is in his mid 50s.
• Walter and Matthew from The Walking Dead: Season Two. While their ages aren't specified, Matthew seems to be in his late twenties-late thirties, while Walter seems to be about sixty.

Web Animation

• Tanabata Manga:
  • Saki finds out that her boyfriend Tomoya is also dating her mother, Noriko. When Saki tries to warn Noriko about Tomoya's two-timing, she brushes it off and keeps her relationship with him ongoing. This causes Saki to expose the couple at their wedding.
  • OP's mother, who is 50-year old, is cheating on OP's father with a 29-year old man. When OP's mother is confronted by her husband and children for her affair, she says that she met "the man of her dreams", just because she hated working as a housewife. Years later, OP's mother comes back and begs OP's father to let her back into the family again after she was dumped by her "man of her dreams".

Webcomics

• In Evon Traveller and Lanna, respectively the oldest and youngest members of The Cabal, spend a fair amount of time in the bedroom. He's over 800, she refuses to tell anyone her age but if she's like the others she would be close to 100 at least.
• Lore Olympus features Hades, who is confirmed to be at least 2019 years old, when the story starts, romantically pining for the just freshly turned 19 years old, Persephone. He doesn't realize the age gap at first becuase in the setting Gods and Titans stop aging after a certain point. He's at first chewed out for it by their mutual friends as they think he's trying to take advantage of a younger woman. After some initial panic on his part and assurance he had no idea, most of the supporting cast grow into the idea of them being together because they realize he's genuinely smitten with her, and she's equally so with him though both hide it from the other at first.
• True Villains: There are signs of mutual interest between Sebastian, who's 23, and Elia, who's an 87-year-old that maintains her strength with Necromancy and steals young women's skins to keep her youthful appearance. Sebastian is startled to learn her real age, but no less interested.

Western Animation

• In The Animals of Farthing Wood, during season 3. Owl leaves the White Deer Park Animals to find a mate, during her journey, she meets and falls in love with a male owl named Hollow. The difference in age is that she is an old owl, while Hollow is a young adult owl, and despite the age difference, the two owls fall in love and become an inseparable couple. In the end the two owls fly together returning to the White Deer Park Animals to help the animals of Farthing Wood in the battle against the invasive rats.
• One Goodfeathers segment on Animaniacs had Pesto's mother dating a younger seagull. It was actually implied that said seagull was younger than Pesto, and his insistence on calling Pesto "son" infuriated him to no end.
• The Box: The old man at the bar with the weird animal in a box meets, kisses, and leaves with a much much younger woman, who also has the same kind of weird animal in a box.
• In The Cleveland Show, it was revealed that Lester's wife, Kendra, was his guidance counselor in high school, who convinced him to drop out and marry her, though ironically her obesity combined with his poor hygiene makes him look older and her look younger. While one episode had him feel like she doesn't respect him enough, and he's said to go to brothels instead of sleeping with her due to her obesity, they're depicted as fairly happy together.
• Family Guy:
  • The subject behind episode "Brian's Got a Brand New Bag", where Brian is ridiculed for dating a 50 year-old woman instead of the hot bimbos he usually goes after. She didn't look 50 though, at least not until after she broke her hip.
  • Brian had a romance with an elderly woman he was forced to help take care of until he unintentionally causes her to get struck down.
• Futurama:
  • There's one episode where everyone is given three hundred dollars, so Farnsworth, who is in his triple digits, uses it to get stem cell treatment to temporarily de-age him, resulting in him dating a young punk chick. In the end, she reveals she too took stem cell treatment to temporarily make her skinny and attractive, so when both their treatments wore off, they decide to just go with it.
  • In "The Late Philip J. Fry," after Fry disappears in time and is thought to be dead along with Bender and Farnsworth, a much older Leela eventually marries Cubert Farnsworth. The relationship doesn't last and it's implied he's moved on with Amy.
• Gargoyles: Fox's mother and father, Anastasia and Halcyon, are a subversion. At first, her mother seems quite younger than her father, though we learn that Halcyon, while aged, isn't as old as he looks, he's just decrepit from disease, and when we see them when they were married they looked the same age, and Anastasia just didn't age as fast. Then there's the reveal of Anastasia as Titania makes this a case of Mayfly–December Romance as she doesn't age at all.
• Kim Possible: Dr. Drakken (who is the same age as Dr. James Possible) and Shego (who is in her mid to late 20's). They are established as a couple at the end of the series.
• King of the Hill: Cotton Hill, Hank's father, and his second wife, Didi, who was actually in Hank's kindergarten class when they were kids. They even have a son together.
• The Simpsons:
  • Mr. Burns once fell in love with a girlfriend of Snake's. She appears to be in her late twenties to early thirties, and his age is probably over one hundred. They had several dates in the episode, but she ultimately returned to Snake.
  • There was a significant romance with Comic Book Guy (in his late twenties, early thirties) and the elderly Agnes Skinner. He was arrested for the possession of illegal videos at the end of the episode, and Agnes told him she wouldn't be waiting for his release from prison.
• The Smurfs (1981):
  • In the episode "Romeo And Smurfette", elderly Papa Smurf (along with the other Smurfs) starts having thoughts about marrying Smurfette, but she even turns her peers down by stating that she's still too young and that she loves all her fellow Smurfs equally.
  • In the episode "Papa's Wedding Day", older Papa Smurf has a romance with the young and beautiful Flowerbell the woodnymph... who turns out to be an infiltrator sent by Balthazar to capture the wisest Smurf of all.
• Teen Titans has Raven's crush on her teacher Malchior - she's about 15 years and his age is at least three digits. An easily overlooked example because he's a dragon posing as a white haired young-looking guy - a phenomenon often observed in Mayfly December Romances. Also, he's made of pages from the book he's trapped in, which serves to distract. Whether or not that relationship would qualify as a Mayfly–December Romance is uncertain, due to the natures of the characters.
• Tom & Jerry Kids: In the episode, "Dakota Droopy Returns", Droopy and Dripple are on a quest to rescue a beautiful young jungle princess, but they discover she has already been rescued by Grandpa Droopy and two have since gotten married. And the beautiful young princess is now Droopy and Dripple's new grandma.

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