The Real Life, mundane version of the Mayfly-December 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:
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.
Keep in mind that for a true May-December romance, one of the partners must be in the "winter" of life, that is, in the "senior citizen" range, while the other is in "spring." You might find the idea of a 40 year old dating an 18 year old to be squicky, but it's not a true May-December romance because a 40 year old is not in the "winter" of life. Even the child being underage (definitely the "spring" of life), doesn't automatically make the relationship a May-December romance. Similarly, a 65 year old dating a 40 year old isn't a true May-December romance, because a 40 year old isn't in the "spring" of life, either. As a rule of thumb, look at the picture on this page. See how the man might be mistaken for the woman's grandfather? That's a May-December 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 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.
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.
Quite obviously Truth in Television, or else we probably wouldn't have a well-known phrase for it. In older periods, before romance became a major part of marriage and courtship, it was even more common. Men would try to become economically established before marrying, while women would (due both to fertility being higher at a young age, and motherhood being the primary female occupation) get married much younger. Ten to fifteen years' difference was considered normal. Once again, this is an Objective Trope, and should not be subject to Values Dissonance.
See also Lolicon and Shotacon for when folks go after much younger partners, as well as Christmas Cake 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, and almost inevitable with Parental Incest.
There is consideration for a "lite" version of this, the May-September Romance, where the age gap is around 20 years, but this is still under debate. Examples on this page must meet this trope's criteria.
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Anime and Manga
Noriko and her husband university professor Tetsuya Ukai in Gravitation
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.
Kare Kano: Sakura Arima, daughter of Yukino and Soichiro Arima. In the last chapter of the manga she confesses her love to Hideaki Asaba, her parents' close friend since high school; even though she is only 15 at the time, it is implied that Hideaki shares her feelings.
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). Rin eventually falls in love with Daikichi, who is 24 years older than her. She follows through on those feelings when she learns that she isn't actually related to Daikichi by blood.
Strike Witches has Wilma Bishop, who married a man much older than herself.
A one-sided version of this trope is used for laughs. Doctor Tofu is a licensed chiropractor who has been practicing as a professional for years (and who may be over 100 years old). He's in love with Kasumi Tendo, a 19 year old girl, and has been since she was in Junior High. Kasumi isn't aware of it, primarily because Tofu is so infatuated that the mere sound of her voice turns him from a practical, level-headed person into a flipped out weirdo who can be a danger to himself and everyone around him with his mindless antics. Even though Kasumi gives no sign of even being aware of Tofu's feelings, never mind reciprocating them, Akane believes that Kasumi and Tofu are destined to be together, and considers the idea "cute". Word of God, via the memorial book and its love chart, is that Dr. Tofu's feelings are onesided.
Played for laughs later on 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?!
There's Maison Ikkoku, where Kyoko's husband Soichirou was also her teacher at high school, but he died not long after the wedding and her own parents at least once expressed distaste with Kyoko having married him in the first place. Later, when Yusaku Godai becomes the target of a Precocious Crush by his own student, Ibuki Yagami, he is disgusted by and quite disapproving of the idea.
In the Blue Drop anime, there is the relationship between the two main characters. Hagino is quite a bit older than Mari, since the Arume don't age as fast as human beings— the relationship between them would have become a Mayfly-December Romance if Hagino wouldn't have died in the end. In any case, Hagino was already looking the same age when she arrived on earth five years earlier and was by then already an experienced space ship commander.
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.
Ian Vashti and his wife, Linda, in 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.
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).
Used for Tohru's parents in Fruits Basket. Katsuya Honda was a student teacher when Kyoko Katsunuma was still in middle school and he became her Big Brother Mentor, helping her to heal from her severe emotional troubles. He deliberately held off until she was out of school to propose to her. And he did that right on time, since when he went to talk to her, Kyoko's Abusive Parents were throwing her out of home for being a delinquent and bringing them bad rep. Katsuya then gave them a What the Hell, Hero? speech and took Kyouko into his home.
Also probably applies for Akito and Shigure, since Shigure was shown as a little boy when Ren was pregnant with akito..
Van Hohenheim and Trisha Elric of Fullmetal Alchemist. Even if you factor out Hohenheim being a 400 year-old immortal, there's still the fact that Hohenheim looks to be in his late 30s/early 40s and the databooks put Trisha at 26 when she died, meaning she had Ed when she was roughly 21.
A very strange version occurs in the 2001 Nights short story "So Brief, So Lasting a Love". Decades after her husband is sucked into a black hole and finding out she finds out she's dying from a disease, a colonist receives word that the black hole that had sucked in her husband has returned. Due to the effects of the black hole on space-time, he's still in there and he hasn't aged a day. She is quickly shuttled to the black hole for them to be reunited for the last 60 seconds of their life... a minute that will last an eternity for those on the outside looking in. Awwwww...
Another short story has what appears to be this between an older man and a younger woman... only it isn't. She's his mother, and she's been aging much slower due to the twin paradox.
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.
Howl's Moving Castle: Howl and Sophie are an example in both ways: he's 27 and she's 18. Or if we take the aging curse into account, he's 27 and she's temporarily 90.
In the movie only, the curse is a bit more mutable with regards to age. Sometimes she's about 60, depending on her mood, but that's a moot point as 60 is still more than twice 27.
In Chrono Crusade, 16-year-old Rosette is sweet on er Parental Substitute Father Remington, who publicly claims to be 27 and is actually at least 72. Her partner and primary love interest Chrono is at least as old as Remington, despite appearing to be a 12 year old through most of the series.
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.
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.
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.
Luffy and Boa Hancock. Luffy is in his late teens and Boa is somewhere in her thirties. On top of that, she's also six-foot three while Luffy is a few inches under the six-foot mark.
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.).
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.
She has at last found an age-appropriate partner in the sprightly octogenarian James Barnes.
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 Green Arrow dated was always the original's daughter, and Green Arrow was now at least a decade older than her.
A recent flashback has shown Dinah in her teens during the mid-nineties, putting her around her late twenties; by contrast, Ollie is at least fifty.
And in still another 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 Mayfly-December 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 Mayfly-December 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 early 1940s or the late 1930s, when he was in university and she was 17, a difference of only ten or so years.
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.
Fairy Tales and Folklore
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.
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.
Harry/Voldemort or Harry/Tom Riddle ship. Voldemort is at least 50 something years older.
For a more subtle version, 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, Fridge Logic says 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 (50+ gap).
Any Yami No Matsuei 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.
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.
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 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 2.
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.
The Lord of the Rings: Aragorn and Éowyn, but only by a few decades. Less tension, which is quickly defused when Faramir comes on the scene.
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.
Tom Greer (Bruce Willis) and Maggie Greer (Rosamund Pike) in Surrogates 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 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.
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).
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 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).
Also many relationships among Howard Families members, where spouses can differ in age by centuries, but this is hard to tell, as the actual lifespan of folks is variable.
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 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 timenote 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.
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.
Dorothea Brooke marries the middle-aged Rev. Casaubon in George Eliot's Middlemarch, much to the consternation of some younger men.
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 married the 18-year-old Queen Ehlana to her fiftysomething-year-old knight-protector Sparhawk. Genuine love match on both sides. And then Sparhawk's boyhood friend (late 50's) marries the maid (18). Also the case with Polgara and Durnik in the Belgariad/Mallorean series, although Durnik being made a sorcerer, with the extended lifespan that comes with it keeps it from being a Mayfly-December 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.
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 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.
This happens in The Dresden Files book 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.
Sort of offset insofar as a previous encounter with a body-switching sorcerer left Luccio permanently in the body of a twenty-something woman.
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 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.
In Gene Stratton Porter's 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 Chad Harbach's 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 Pearl S. Buck's 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.
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.
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.
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.
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.
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.
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 he mid-to-late thirties, but she's treated as if she was in her twentiesnote 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.
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.
Later re-done, sort of, with Edith and Michael Gregson. Gregson is in his late 40s or early 50s, so it's not quite here, but the similarity to Sir Anthony is uncanny in many ways.
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.
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.
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 SitcomMay 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.
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 OperaRomane. 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.
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 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.
Doctor Who: The Doctor's clone-grown-from-a-severed-hand and Rose. She's in her twenties; depending on how you count the clone he's either a few days old or over 900 years old.
In Veronica Mars, Lilly Kane had a fling with her on-and-off boyfriend Logan's father Aaron (a famous actor). When she found out Aaron was videotaping their "encounters", she stole the tapes and hid them. When he came over to demand the tapes back, she threatened to give them to the press. In a fit of rage, he killed her and ran away.
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.
For a Japanese song referring to this trope, look no further than 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.
Tom Lehrer mentions this at the end of his song "When You Are Old and Gray".
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.
"Young Girl" by Gary Puckett and The Union Gap. The narrator is horrified/angry/bemused when he finds out that his lover is underage, but it is possible that he doesn't end the relationship. Instead, he begs the girl to walk away. It's a reasonable guess that she doesn't.
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.
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 2000, Mark Henry had an infamous romance storyline with 80-year-old Mae Young.
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.
Religion and Mythology
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, Jesus'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 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.
Also in H.M.S. Pinafore, in which Captain Corcoran marries Buttercup, his nurse when he was a baby. Oh, and since Ralph Rackstraw is Corcoran's age and Corcoran is Josephine's father, Ralph is marrying a woman young enough to be his daughter.
Pirates doesn't quite qualify, as Ruth is explicitly stated to be 47 when Frederick is 21. However, regardless of the age of the actress portraying her, she's often made up to appear significantly older than 47, since it's pretty clear that she hasn't aged well: as PK states, "There are the remains of a fine woman about Ruth."
It probably happened in the back story too: if Emile's (deceased, native) wife was anywhere near his own age, the fact that their children are still, well, children and not approximately Nellie's age is a minor medical miracle.
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.
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 Connomore, who worked for Miranda's father and then swore loyalty to her.
This may be also the case between Gregor (age isn't explicitely spelled, but he seems to be in his late 30's/eaely 40's) and the marriage-able ladies in the Chrom's Shepherds group save for Nowi (the girls's age ranges seem to go from mid-teens to early/mid 20's as well.)
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.
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.
The Simpsons, as one episode shows that Apu is significantly older than Manjula. Also, Mr. Burns also fell in love with a girlfriend of Snake's. She appears to be in her late twenties to early thirties. He also once dated Marge's mom, who is at least in her sixties so its not as notable, but he's, at his youngest, in his eighties, but depending on the writer he's sometimes around 160 years old. He also attempted to have one with Marge, didn't work though.
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.
Though, they might have dated much younger then that.
One Goodfeathers segment on Animaniacs had Pesto's mother dating an older pigeon.
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.
And in The Cleveland Show, it was reveled that Lester's wife, Kendra, was his guidance councilor 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.
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 Mayfly-December Romance as she doesn't age at all.
James Woods (67) dated Ashley Madison (27) for seven years. Before that, he was with Danielle Panabaker (26), who played his daughter on the television series Shark. He is currently dating Kristen Baugness (20).
Charles Dance (67) once dated Sophia Myles (32), and was engaged to Eleanor Boorman (39).
Aisha, one of several wives of the prophet Muhammad, was 45 years younger than him. However, that one was an Arranged Marriage with strong political overtones: Aisha was one of the younger daughters of his best friend/sidekick/Number Two/eventual successor Abu Bakr al-Siddiq.
Tenth U.S. President John Tyler was 54 when he married his second wife, 21-year-old Julia Gardiner (who agreed to marry him after she fainted into his arms after seeing her father die when a naval gun blew up) . She was younger than three of his eight children by his first wife, and they had seven more together.
Lyon Tyler (John Tyler's son) married his second wife when he was seventy (with a thirty-five year age difference). The end result is that there are still grandchildren of John Tyler's alive today.
Victorian Edward Burne-Jones, pre-Raphaelite painter and British designer of stained glass. When he was 58, Burne-Jones met and fell in love with a 35-year-old married woman. In his letters he apologised to her for being so much older and said he would understand if she looked for a younger suitor.
Lord Baden-Powell, founder of the Scout Movement, married 23 year old Olave St. Claire when he was 55 (though, incidentally, they shared their birthday: 22 February).
William Randolph Hearst was 56 when he began to live openly with his mistress, Marion Davies. Davies was 22 at the time. This affair lasted till the end of Hearst's life.
Charlie Chaplin's last marriage was to a 18-year old woman, Oona O'Neill, when he was 54 years old. They lived happily together until he died in his sleep at the age of 88. His previous three wives were also much younger than him.
Raissa Myshetskaya went to the Paris Conservatory to study music and married her teacher, Ernest Boulanger, 42 years her senior. They had two daughters, Nadia and Lili Boulanger. Their father was seventy-one when Nadia was born and seventy-six when Lili was born.
Conservative politican Baron Boothby's second wife was thirty-three years younger than him (67 and 34, respectively).
When he was 87, Arthur Miller began living with a woman who was 55 years his junior: minimalist painter Agnes Barley. Two years later, Miller announced that he was in love with her and that they intended to marry. Barley was with Miller when he died not long after this, aged 89.
Advice columns, including (but not limited to) "Annie's Mailbox," "Dear Abby" and others frequently publish letters from readers seeking advice about May-December romances. Frequently (but not always), the letter will be from a family member of the younger half of the couple who is concerned about the age difference; the situations vary widely. The take of the "Annie's Mailbox" editors has usually been that, so long as both sides are at least 18 and consent and are not married, there is little that can be done except to offer love and best wishes.
Hugh Hefner. Specifically his wife (who initially bailed five days before the wedding but is later reconciled with him), Crystal Harris, is a full sixty years younger.
72-year-old Italian Prime Minister Silvio Berlusconi has been paired with numerous women, most notably 18-year-old model Noemi Letizia. Naturally, this has caused something of a stir. In 2012, he announced his engagement to a woman who is 49 years younger than him. (She's 27.)
The late Anna Nicole Smith (age 26 at the time) married oil magnate J. Howard Marshall when he was 89.
Billy Joel married 23-year-old Katie Lee. At the time of the wedding, Joel was 55. Joel's daughter, Alexa Ray, then 18, served as maid-of-honor.
Keith Carradine (b. 1949) and Hayley DuMond (b. 1974) fell in love on the set of The Hunter's Moon, in which their characters also had a May/December romance.
Nip/Tuck star Julian McMahon is the product of one of these relationships. His father, Australia's 20th prime minister William McMahon, met an occupational therapist named Sonia Hopkins before he became prime minister. When the two got married, William was 57 and Sonia was 32. (Sonia McMahon would later create a scandal by wearing a revealing dress during a visit to the Nixon White House, FYI.)
The 2011 marriage of actor Doug Hutchison (54) and aspiring singer Courtney Stodden (19) with parental approval. They divorced in 2013 (citing the age difference as the "huge major" reason), but are still living together. In 2014, they announced they were to re-marry.
Through the power of this trope, a few widows of American Civil War veterans lived into the 21st century. In all known cases of this, the brides were in their late teens or early 20's, and the marriages happened in the 1920's and 30's when the grooms were quite elderly. The last living Confederate widow, Maudie Hopkins, died in 2008. The last known Union widow, Getrude Janeway, died in 2003, receiving her husband's bi-monthly pension check of $70 until her death.
Yassir Arafat was 34 years older than his wife Suha (they married when she was 27 and he was 61). From all appearances, they were happily married until his death in 2004.
Strom Thurmond's second wife was 44 years younger than him. They married in 1968 when he was 66 and she was 22, had four children, and despite separating in 1991, remained married until his death in 2003.
Bobby Liebling, singer of cult-metal band Pentagram, is 33 years older than his wife Hallie, and they currently have one son together.
General Douglas MacArthur had a relationship from 1930 to 1934 with Isabel Rosario Cooper, whom he met when he was 50 and she was 16.
US Congressman Dennis Kucinich met his third and present wife when he was 59 and she was 28.
The third wife of the late James Doohan (of Star Trek fame) was 36 years his junior. They were married when 54 and 18, respectively.
Most considered the marriage of Canadian Prime Minister Pierre Trudeau to Margaret Sinclair to be one of these. At the time of their wedding in 1971, he was 51 and she was 22—their age gap was a little over 29 years. Unfortunately, she had believed his public image that he was "young at heart" and although he was certainly eccentric and loved jokes, he was also a workaholic with little time to actually go and have fun (not to mention that he was Prime Minister of Canada, which is apparently an extremely time-consuming job even if you aren't a workaholic—apparently, Canada is unusually hard to govern despite appearances), and she was bipolar, and so they divorced nine years later. They did have three sons, however, of whom their eldest, Justin, is currently Leader of the Liberal Party.