"Some say I'm robbing the cradle, but I say she's robbing the grave!"The Real Life, mundane version of the MayflyDecember Romance. 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:
— Hubert Farnsworth, Futurama
- As the result of successful Wife Husbandry.
- Teachers and students. (Obviously, if the teacher is very young themselves, the difference might not be so great).
- 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.
- 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.
- The individuals should be of approximately the same lifespan. Otherwise, it's a MayflyDecember Romance.
- Presuming Human-normal lifespans, the older needs to be at least 55
- Similarly, the younger can be no more than 40
- There needs to be at least a 30 year gap in age between the two
- The ages are from when the relationship started. If a 50 year old and a 85 year old are a couple, this trope would qualify if they've been together for 20 years, but not if they started dating last week. (Minor exception: The other way around—if a 60-year-old and a 30-year old have been together for ten years, for example—is a bit fuzzier, since let's be honest the younger the younger one is, the lower the age of the older person has to be for it to be odd.)
- 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, he's 30, not 130, for the purposes of this trope.
- For creatures with extended (or very brief) lifespans, apply the above rules generally. The older should be vastly more experienced than the younger in practically all ways. For example, a 1000 year old vampire dating a 100 year old one would apply this trope, but not if dating a 500 year old one.
- The difference has to be noted in Universe as an unusually large age gap. For live-action media, the actual ages of the actors/actresses are immaterial, it's the age of the characters that matter.
- This is a Romance Relationship trope. There has to be an actual romantic (whether real or fake) relationship of at least a modest length to qualify; brief flings or one-off encounters don't qualify.
open/close all folders
Anime and Manga
- 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.
- 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.
- Several of these relationships are seen in Detective Conan... 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 example, we have the writer Daisuke Torakura (in his 50's) and his wife Etsuko (mid 20); 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 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.
- 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 Ai ON. 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.
- Yoshihara Yuki's josei comedy manga Itadakimasu; with the main couple being a middle-aged OL (office lady) in a relationship with her ex-husband's younger brother, who happens to be in high school for the first half of the manga. The fact that he's been in love with her since she married his brother, when he was in junior high, makes it even moreso.
- Midori in Mai-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.
- Ian Vashti and his wife, Linda, in Mobile Suit Gundam 00. Ian is even called out on how young his wife is, causing him to defensively note he waited until she was legal to marry her (or try anything else), before demanding they focus on the important reasons they're there and not on his young wife. They are 57 and 32, respectively, in the second season (which is when Linda first appears); it's also worth bearing in mind that they have a 14-year-old daughter, the Bridge Bunny Mileina.
- Mobile Suit Crossbone Gundam has Crux Dogatie and his unnamed first wife, who died some time 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.
- The Secret Garden: In the anime series Lillias was much younger than 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.
- 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.
- Daimaru Nakajima who is a Cool Old Guy and his second wife Senna in You're Under Arrest!. Senna is younger than Daimaru's son Ken...
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.
- Natalia Romanova (the first Black Widow) and every modern-age character she was ever involved with. She was born shortly before World War II, but thanks to some unspecified procedures she underwent during her time with the KGB, her aging process has been slowed. The stories don't usually mention this, because, well, the prospect of Daredevil, Iron Man, or Hawkeye being involved with someone old enough to be their grandmothers was bound to squick somebody.
- In another DC Comics example, 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.
- In DC Comics example, 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.
- 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.
- In the dystopian divergent timeline of the Age of Apocalypse, where Magneto became the earth's greatest superhero and founded the X-Men, he and Rogue eventually married and even managed to have a son. This was still controversial among fans because they initially had a surrogate father-daughter relationship, because he mentored her in the use of her powers after she permanently absorbed the powers and part of the psyche of his own secretly long-lost biological daughter Polaris. However, at the time Age of Apocalypse was written, Polaris was established as not being Magneto's daughter. This was only reversed by Retcon some years later, after a lot of the controversy had died down. They also married in another timeline, another of their children appears in the Exiles. And they've finally brought this relationship into the main Marvel universe, after teasing it many years ago.
- 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. Occasionaly it verges into May-September or MayflyDecember Romance territory as characters are rejuvenated through comicbook-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. The chronological age difference is even more pronounced in the case of many of the romantic entanglements of Wolverine and Mystique, both of whom are canonically over 100 years old. In Logan's case Jean Grey, Mariko Yashida and Yukio were in their twenties and Melita Garner is probably in the same age-group. Mystique had an affair with Iceman, the youngest of the original five X-Men, which left her with fairly strong lingering feelings. On a more mundane level, there was Cannonball (16 years old at the time) and rockstar Lila Cheney.
- This happens to Sue Storm a lot; she's had feelings for the eighty- to ninety-year-old Namor, with a touch of MayflyDecember Romance (he's not immortal, but he is longer-lived than most humans.) Despite appearances, however, Sue and Reed aren't this: using the the original timelines, Reed met Sue in the mid or late 1930s, when he was in university and she was in her teens, a difference of only ten or so years. (John Byrne later said she was 12, which is why they didn't get together until after the war, Matt Fraction retconned this to her being 17, with Tom Breevoort explaining that the Byrne version, in 2013, struck the editorial team as "more than a little creepy").
- In Top 10 by Alan Moore, we learn in the backstory The Forty-Niners that this was the case when Captain Traynor ("Jetlad" at the time) and his partner got together. They're now both old men, so the gap isn't really noticeable anymore, but at the time Traynor was still in his teens.
- While this is definitely the least of the problems concerning their relationship, Joker is generally depicted as a man nearing his fifties (though everything about him is an uncertainty, so for all you know, he could be around her age), while Harley Quinn is portrayed as a young woman that was a fresh-out-of-college intern when she met him.
- 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.
- 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.
- 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.
- Circles: When they first met, Paulie was in his early 50's and Douglas was in his early 20's.
- In The Ultimates (2015) Monica Rambeau and the Blue Marvel began to date. He is a retconed Korean war era superhero (who first appeared in a 2009 mini series) with extended lifespan and also a widower with several adult children, she is subject to Comicbook time so around her 30s (but with publishing history going back to the 80s). It was even acknowledged when Monica confided Carol Danvers that she wasn't sure about the relationship because of the in-universe age difference.
- Andrea and Dale from The Walking Dead.
- 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.
- 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.
- 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.
- 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 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 borne 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 fanfic around when she was a student qualifies (54 year gap).
- 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.
- 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. And just when you thought this fandom couldn't imagine romantic love without sexuality!
- 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.
- 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."
- TD and Celestia eventually strike up a friendship and later romance in 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.
- In the Card Captor 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.
- 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.
Films — Animation
- 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).
- 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.
Films — Live-Action
- 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.
- Ali: Fear Eats the Soul is another rare example of a gender flip of this trope. Emmi, a cleaning lady well into her sixties, finds love with Ali, an African immigrant no more than half her age.
- Verfolgt (Hounded / Punish Me). 16-year-old boy and 50-year-old woman. She is a probation officer. He's one of her cases. It's a BDSM relationship, she dominant and he submissive.
- 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, specially 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 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.
- 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 face lift Doc mentioned getting in Part II.
- 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.
- 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.)
- 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.
- In Memoirs of a Geisha, we have Sayuri and the Chairman, who is roughly twenty-eight years older than her.
- In Leonard Part 6, Leonard's daughter dates her theater director. Leonard says he's old enough to be his father.
- In Les Demoiselles de Rocherfort ("Young Girls of Rochefort"), Solange falls in love with Andy. Just to underline the age gap, Andy's childhood friend Simon gets married with 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.
- 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).
- Fred Astaire, who didn't begin his film career until he was a well-established stage star in his thirties, was often paired with younger and much younger leading ladies. He was twelve years older than his most famous costar, Ginger Rogers; twenty-two years older than Judy Garland in Easter Parade; and a whopping thirty and thirty-two years older than Audrey Hepburn and Leslie Caron, respectively, in Funny Face and Daddy Long-Legs. But, after all, he was Fred Astaire.
- In Wild Target, the 55-year-old Victor ends up with the 27ish-year-old Rose.
- 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 Jegen Prochnow) and Damiana (played by Blanca Jara who was 23 at the time).
- While this appears to be the case in Red with between the 60ish 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 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.
- The 1973 film Breezy has 19-year-old Breezy fall in love with the bitter 54-year-old Frank Harmon.
- 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.
- Last Vegas: Billy and his bride-to-be. He's 70 and she's 31.
- 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 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.
- The plot of Manhattan involves middle-aged Isaac Davis dating 17-year-old Tracy, something that's been cited as the reason why it's rated R by the MPAA.
- 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 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.
- 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.
- Vincent and Daka show signs of this in St. Vincent. Vincent was old enough to have served in Vietnam; Daka is young enough to have the ability to conceive his child.
- Between Leo the aging two-bit gangster and his much younger, sensual neighbor Sally. When Leo is about to take a bus out of town, Sally gets the bus driver to force him off by claiming that Leo 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.)
- Prime Cut: A 50 year old mobster (Lee Marvin) falls for a barely legal hooker (Sissy Spacek).
- 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.
- 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!!?
- 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).
- In Rafael Sabatini's Scaramouche, the Marquis de La Tour d'Azyr is easily old enough to be Aline's father. After all, he is Andre Louis' father.
- While strictly speaking a MayflyDecember 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 timenote 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.
- Dr. Strong and his much, much younger wife Anne in Charles Dickens' David Copperfield.
- 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.
- Although the age difference doesn't seem to be as pronounced, Mr. Dombey's second marriage in Dombey and Son.
- 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.
- Wilkie Collins' Man and Wife concludes with the marriage of Anne Silvester and Sir Patrick Lundie, although Sir Patrick is decades older.
- 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.
- A few P. G. Wodehouse stories have done this, where a woman previously engaged to a man winds up marrying his uncle (or, in the case of one Reggie Pepper story, widowed father).
- 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.
- David Eddings:
- 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).
- 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 MayflyDecember Romance.
- 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.
- Played with in The Time Traveler's Wife. Henry and Clare have a bit of a May-September Romance in the 'normal' timeline with him being about seven years older than her, but during his involuntary time-travel trips to her youth, she falls in love with him gradually over the ages of six to eighteen while his age varies at random but is generally in the late twenties or early thirties. This, fortunately, avoids any sex until Clare's eighteenth birthday, though she demands kisses from him in her teens.
- 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 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 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.
- 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.
- In Memoirs of a Geisha, Sayuri is in love with the Chairman, who is twenty-eight years older than her.
- Hannibal Lecter and Clarice Starling from the The Silence of the Lambs series. He's 19 years older than her (though Thomas Harris engages with a lot of timeline wonkery through out the books). Though, for most of the series, their "relationship" is hardly a romance.
- A favorite trope of Danielle Steel, and one where she frequently displays a blatant Double Standard. However, the Double Standard is not based on gender, but rather the type of character—a hero/heroine can easily date or marry someone 20-25 older/younger—or in two extreme cases, 40-something years older. Even a virtual case of ephebophilia was presented as a romance—a 40-something year old man and a 16 year old girl (she was his daughter's best friend) fell in love and planned to marry as soon as she turned 18. Meanwhile, a villain is said to look ridiculous dating someone a mere 15 years younger than him.
- 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.
- 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.
- In The Phantom of the Opera, Christine is between 17 and about 21. Raoul is 21 or so. Erik is 50-something at least.
- Deconstructed with Altisidora and Don Quixote in the second part: Altisidora, a 14 year old maiden at the Dukes 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 shes 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 Altisidoras feelings caused him more confusion than pity.
- 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 poem "Poltava" by Alexander Pushkin offers a particularly twisted example, though the exact age gap is left unstated, other than "significant".
- In Devon Monk's Allie Beckstrom novel 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.
- 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.
- 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.
- In the Girls series by Jacqueline Wilson, Ellie's father is in his 50s while his wife Anna is in her late twenties to early thirties. Anna used to be one of the students he taught in a college class.
- In Katy, by the same author, it's noted that Katy's middle-aged father is much older than both his wives were.
- 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.
- 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 Wild Swans, 25-year-old Yang Yu-fang marries Dr Xia despite a forty year age gap and the vociferous protests of his family.
- 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.
- In you could make a life, the 35-year-old Mike is very reluctant to get into a relationship with the sexually inexperienced 18-year-old Liam who looks even younger than his age. The fact that the age/size difference actually turns Mike on makes him feel even dirtier. Even when he inevitably gives in to Liam's persistence, he lives with the constant belief/fear that Liam will eventually outgrow his crush on him. He doesn't.
- Reena's father's second marriage from The Poison Apples. He's in his fifties and his second wife is in her twenties.
- 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 Oliver Twist, it's implied by Mr. Brownlow that Oliver and Monks's father Edwin Leeford and his unnamed first wife aka Monks's mother were like this. Uncommonly, she was the older one. And theirs was a very unhappy union.
- In The Rogue King, Koral is thrice Lasil's age and, presumably, has only ten more years to live.
- 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.
- 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.
- 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.
- 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 the Warrior Cats prequel Bluestar's Prophecy, Pinestar and Leopardfoot have kits some time after Leopardfoot becomes a warrior. Pinestar was already a leader on or close to his last life when she was born.
- In the Colleen McCullough novel Tim, the mentally disabled title character falls in love with the woman who has employed him as a gardener, despite the fact that she's at least twenty years his senior.
- 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 The Small Things: middle-aged musical director Michael and young soprano Layla.
- 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.
- Series/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.
- Beverly Hills 90210: In the episode "Wild Horses", Dylan enters into a brief affair with a woman at least 20 years his senior. It's not stated how old she is, but it's roughly late 40s/early 50s.
- HBO's Big Love gives us all the creepy Juniper Creek couples, the creepiest of which is definitely 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.
- Community: Jeff/Annie are technically an example, but it gets downplayed, as all their Ship Tease is when Annie is acting more mature, and Jeff is notably turned off whenever she acts like a child. It helps that Annie's actress is eight years older than the character, so the age difference isn't actually that big. Evil!Jeff and Evil!Annie from the Darkest Timeline play this up, with Evil!Jeff saying he wishes the age difference was larger, and Evil!Annie saying she likes it when he talks down to her like a child.
- An episode of the The Cosby Show had a 53-year old colleague of Cliff's introducing him and Clair to his early-to-mid twenties new girlfriend. 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.
- Grissom and Sara on CSI. To make things potentially squickier, he was also her supervisor.. Though, this might not qualify, as Grissom is at most in his early 50s, and Sara is either late 20s or early 30s.
- 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 twentiesnote . In season 2, she starts an Office Romance with a much older Agent Lundy (in his sixties) who could easily be her father.
- Doctor Who has had the lead character, the Doctor, occasionally enter into romances with travelling companions and others. Due to the Doctor's immense lifespan, the difference in age is always in the hundreds if not thousands. An example is Rose Tyler, who is 19 when she first meets the Doctor, who is approximately 900 years of age. Later, when the Doctor is well over 1,000, he marries River Song, who is said to only be a couple of hundred years old. The age gap between the Twelfth Doctor and Clara Oswald when their relationship ends can technically be measured in the billions (as is also the case when the Twelfth Doctor later reunites with River).
- Downton Abbey: Lady Edith Crawley (in her 20s) and Sir Anthony Strallan (in his 50s, and widowed). Within her family, this was actually considered a fairly decent match for Edith before the War, in large part because her family thought Edith, being "less pretty" than her sisters and a bit tomboyish and abrasive to boot, couldn't do any better than a middle-aged widower. After the War, though, Sir Anthony came back with a crippled arm, and the family decided—and Sir Anthony recognised—that the match was no longer any good, as Edith would have to be a nursemaid to him rather than a wife. Edith refused to believe this until Sir Anthony jilted her at the altar.
- 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.
- On Empire, Hakeem, who is in his early twenties (judging by the fact that he was a baby when his mother went to jail in the '90s) and Camilla, a middle-aged fashion designer. His parents are not pleased.
- Deconstructed in one episode of Frasier where a young woman in her early twenties (played by Sara Melson) is interested in dating Frasier, but he is worried that people would have bad impressions of him. Finally invoked near the end of the episode, but they decided that it won't work out.
- Friends: Monica's boyfriend Richard was "a person who can drink" older than her and friends with her parents. His friends are impressed that hes dating a twinkie. They eventually broke up because they were at such different stages of their lives, and she was much happier after falling in love with her best friend who was her own age.
- Monica: I used to pee in your pool!
- In the made-for-HBO movie The Girl in the Cafe, the eponymous girl (early 20's) falls in love with a 46-year-old diplomat. They are in denial of this until they very end, even though he invites her to a conference in Iceland with him. They pull a bit of She Is Not My Girlfriend until they admit their feelings. Strictly speaking, this doesn't qualify, but, in a bit of a Casting Fail, the diplomat is played by a 56-year-old Bill Nighy, and he looks his age (i.e. the production doesn't down-age him via effects or makeup).
"Well, now I know two things about Iceland. It's where Björk comes from, and it's somewhere it's possible to fall in something very like love..."
- In the British House of Cards, there is a distinctly creepy one between Francis Urquhart (53 at the beginning of the series) and Mattie Storin (23 or 24). She actually calls him "Daddy," and although he's clearly using her for his own ends, it seems both are into this whole father/daughter dynamic for their own, twisted reasons (although we never quite fully figure out what they are).
- In House Hunters International, there was an English couple from Manchester who were searching for a vacation home in Thailand. While their ages were never mentioned, the lady (Julie) looked notoriously older than the gentleman (Mark). They still looked very Happily Married.
- 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.
- 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 snatching from the cradle.
- 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.
- The Prime Minister And I: In this Korean Series, she is 28 and he is 42.
- 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 50's/early 60's) marries a girl in her late teens (Milenka, who's younger even than Jovanka's daughters aka Melquiades's 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.
- Truth in Television on Rome. Caesar is more than thirty years Cleopatra's senior.
- And 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.
- The Twilight Zone (1959) episode "A Short Drink from a Certain Fountain," deals with a 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 Wire has Lester Freamon (50s) and Chardene (mid 20s in-story).
- Invoked Trope in How I Met Your Mother. Ted dates Carly, and while they don't fit this trope (he's in his early 30s, she's 21), she seems to only be dating him because she thinks he's really old (remarking that he "still goes at it like he's in his 50s"). She describes being turned on by watching 60 Minutes with him and playing shuffleboard.
- Also played with with one of Robin's brief relationships — Ted admits the guy was probably in his 40s, but pictures him being much older.
- In Gilmore Girls, Paris dated her much older professor when she was a freshman at Yale. She named this trope word by word when she confessed 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.
- Quinn from Glee was shortly involved with one of her professors at Yale, hinted to be at least middle-aged while she was barely 19. It ended so poorly it chased her away from all men and into Santana's hotel bed .
- Modern Family: Jay is over 60, Gloria is in her 30s.
- 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. 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.
- 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" ("Bamboleo" for the ones who only had heard the Gypsy 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 a "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.
Myths & Religion
- At times Christian art has traditionally depicted Mary as a young woman of about 16 and Joseph as an old man at the time of the Nativity. If one applies historical context to the story, Mary was probably between 14 and 18, with Joseph in at least his mid-twenties. That's the way it was back then. The depictions of Joseph as an old man aren't without basis, though. The fact that Joseph doesn't appear again after finding Jesus in the Temple suggests that he died somewhere between then and the Wedding at Cana. Furthermore, many early Christian sources suggest that Joseph was a widower, explaining the references to siblings of Jesus as the children of Joseph and his first wife (most likely in support of Mary being a perpetual virgin after giving birth to Jesus, according to Catholic doctrine).
- 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.) Some time 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 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 2000, Mark Henry had an infamous romance storyline with 80-year-old Mae Young.
- In 2003, the Torrie Wilson-Dawn Marie feud was sparked by Dawn Marie's May-December (kayfabe) romance with Wilson's (real-life) elderly father, Al. The feud heated up when Wilson died during vigorous sex with Dawn Marie on his "wedding" night.
- Former Smackdown General Manager Theodore Long was frequently romantically paired with much younger WWE Divas. Notable examples include Kristal Marshall (with whom he had an on-air wedding with) and Aksana (who left him for a debuting Antonio Cesaro).
- Warhorses of Letters - Which is far from the oddest thing about this series of letters between two gay horses on opposing sides in the Napoleonic war.
- In the William Shakespeare play Othello, the title character (age unspecified, but getting up there) marries the pretty young Desdemona. Their age difference is one of the many reasons he suspects her of cheating on him: The man he thinks she's sleeping with is closer to her own age. She's actually perfectly loving and innocent, but given that this is one of Shakespeare's big 5 tragedies, you can probably guess what happens to her.
- Jokingly invoked in Princess Ida, where Hilarion mentions being married to Ida at a time when he was twice her age — that is, when he was two years old.
- 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.
- 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.
- Niccolo Machiavelli's Mandragola features the "hot young wife openly cheating on dumb older husband" variant.
- 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.
- 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.
- Fire Emblem has MANY cases:
- Fire Emblem Jugdral: In Thracia 776 there's Olwen and Fred. They get married after the war, and Fred's ending says he got teased often for being older than his wife as well as her former bodyguard.
- Fire Emblem Elibe: A definitive case in regards to Isadora (mid 20's) and Renault (at least in his 50's, though he looks fine for his age.)
- Fire Emblem Awakening: Through SpotPass, this can happen between a female Avatar (not likely to be past either mid/late teens or early/mid 20's at the start) and the Heel Face Turned Emperor Walhart (at least in his mid-to-late 40's, maybe even his 50's. It's even more blatant if the player customizes said Avatar's features to make her look even younger than she actually is or may be.
- Fire Emblem Fates: A Female Avatar (looks are customizable, but she's probably no older than late teens) can strike one with her retainer Gunter (age isn't fully clarified, but going by his Silver Fox looks he's very clearly over 50), the Hoshidan strategist Yukimura (looks younger than Gunter but seems to be in either his late 30's/early 40's), World's Strongest Man Fuga (40's, already the Parental Substitute of a boy in his mid teens) or the Kohga rogue Shura (at least in his mid-late 30's since he was almost surely a teenager when he helped abduct Azura).
- Tales of Symphonia has multiple examples.
- 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.
- 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.
- 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.
- No age is given for the Inquisitor in Dragon Age: Inquisition, but most customization options make them look like they're in their 20s, and dialogue from other characters seems to imply a younger character. While most of the romance options are in their 20s or 30s, Blackwall and Solas both appear to be in their mid-40s, meaning a romance with either of them could qualify as this trope although Solas turns out to be about 200x older than that, making it a May Fly December Romance.
- Played with in True Villains, where ten year old Mia has a crush on Bayn. He's over eighty years old, but has since been turned, physically, into a child.
- In Sinfest, Monique dismisses an old man as seeking this to relive his youth.
- 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.
- 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. They had several dates in the episode, but she ultimately returned to Snake.
- Krusty and his new co-star, Princess Penelope. Their exact ages are uncertain, but Penelope is "under thirty-three," and was a fan of Krusty's show when she was a little girl.
- There was a significant romance with Comic Book Guy (in his late twenties, early thirties) and the elderly Agnes Skinner. He was arrested at the end of the episode, and Agnes told him she wouldn't be waiting for his release from prison.
- "Rome-Old and Julie-Eh" revolves around the romance and marriage of Abe Simpson and Selma Bouvier, their ages separated by nearly two decades. Their marriage didn't work out, due to Abe's senility leading to the ruination of their kitchen and Selma finding her new job as a department manager too stressful.
- 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.
- Tom and 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.
- It's not a romance, but it's evident the mutual sexual tension between Jonesy and Yummy Mummy in 6teen.
- 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 MayflyDecember Romance is uncertain, due to the natures of the characters.
- 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 subject behind the Family Guy 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 also previously had a romance with an elderly woman he was forced to help take care of, until he unintentionally causes her to get struck down.
- In The Cleveland Show, it was reveled 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 hygene 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.
- Any quick fling Quagmire has with a young girl counts, since he's confirmed to be in his sixties.
- 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 were off, they decide to just go with it.
- There's Mom's relationship with Wernstrom in a flashback. Given that Mom is at least the Professor's age, and Wornstrom was his student, she's at least a decade or so older; though, he's not exactly young himself.
- In the Moral Orel episode "Dumb" it's revealed that Joe's father is Dr. Secondopinionson and his mother is Nurse Bendy. They're not currently together though.
- Attempted and thankfully failed in The Smurfs episode "Romeo And Smurfette" when Papa Smurf along with the other Smurfs start having those 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.
- Achieved in the Empath: The Luckiest Smurf alternate timeline story "Papa Smurf & Mama Smurfette", where they eventually marry and even have their only child together.
- Also achieved in the episode "Papa's Wedding Day", where the 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.
- 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 MayflyDecember Romance as she doesn't age at all.
- 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.