May-December Romance



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

- Hubert Farnsworth, Futurama

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:


 * 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.
 * A man who Likes Older Women getting the attention of his love interest.
 * 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. A "lite" version, in which only a few years separate the couple, may be called a May/September romance.

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. 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. To clear up one last bit of confusion that's been cropping up, the fact that one of the participants may be underage (definitely the "spring" of life), doesn't automatically make the relationship a May–December romance. 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.

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 would have been considered normal.

In short, as a general rule it's usually acceptable to date someone half your age plus seven years, a gap which widens later in life.

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.

Anime and Manga
"Ranma: How come I never realized just how beautiful a woman in full bloom could be?!"
 * and her husband in Gravitation
 * An issue (for one of the characters anyway) at some point in the series Skip Beat!, though the difference in age isn't so bad as another random couple being used as an attempt to resolve the issue, in which a student and teacher married once she was finished school...and the teacher was almost the same age as the student's father.
 * Daimaru Nakajima and his second wife Senna in You're Under Arrest. Heck, Senna is younger than Daimaru's son Ken...
 * Maho Izawa and her boyfriend in Kare Kano.
 * As well as Sakura Arima, daughter of Yukino and Soichiro Arima. In the last chapter of the manga.
 * All over the place in Cardcaptor Sakura, as well as a lot of CLAMP's other works.
 * And the cake goes to the X 1999 pairing of Shiryu Kusanagi, a 38 years old hulking giant of a paratrooper sergeant, and 14 years old junior high school student Yuzuriha Nekoi, whom he is the Capulet Counterpart.
 * Toyed with throughout Neon Genesis Evangelion:
 * Fourteen-year-old Rei has beyond-platonic feelings for her guardian Gendou Ikari, who is forty-eight. So far as we know, they never have anything approaching a normal "relationship", but her status as leads to all sorts of Squick and speculation. Meanwhile, one would have to be deaf and blind to miss the fact that Asuka (only thirteen when she's introduced) is infatuated with her former guardian, thirty-year-old playboy Ryoji Kaji. Kaji, however, never reciprocates.
 * As for actual relationships, Gendou Ikari is in a relationship with Ritsuko Akagi (eighteen years his junior). Earlier, he's paired off with Naoko, Ritsuko's mother, who was slightly older than him.
 * Several people—not least Misato herself—make occasional jokes about Misato sleeping with Shinji. But the "joke" runs thin When Shinji yells for her to stop and shrinks away in disgust, she flees the room, apologizing. Soon thereafter, Shinji runs away again, and that's pretty much the last time she's ever entrusted in a position as his "guardian", since later, there's her "goodbye kiss" and accompanying remarks.
 * Nor is it clear how platonic the relationship between Prof. Fuyutsuki and Yui Ikari was.
 * 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.
 * Strike Witches has Wilma Bishop, who married a man much older than herself.
 * Although the gap is significantly smaller than usual—about six or seven years between 14 Usagi and 20-ish Mamoru—it's a big enough deal in the Sailor Moon anime that Usagi worries about her father's reaction. As well, Naru and Nephrite fall in love, prompting Usagi to use his (apparent) age as a reason for Naru to avoid him. In the manga, however, both men are only in their late teens and act their ages.
 * Let's be fair to Mamoru: we're never told how old he is in the anime, only that he is in university - that places him somewhere in the 17-22 age bracket. A flashback in the R movie shows a 4 or 5-year-old Usagi with a not-older-than-12 Mamoru, so the age difference is more of May-September than May-December.
 * Lina of Slayers is 15 when the series starts, whereas her swordsman guardian and eventual Love Interest, Gourry, is 22. Their relationship even starts out as such: he treats her like a child at first, much to her dismay. There is also the sorceress Eris, who appears to be in her early twenties, and her one-sided obsessive love for the priest Rezo, who's almost a century old (mind, he's younger than he looks.).
 * The main couple of Wolf's Rain qualify for this on two levels: Cheza looks to be about 13, but is Really Two Hundred Years Old, and Kiba's human form looks about 20, but he's only about 2 or 3 in wolf years. Either way you slice it, there's quite an age gap.
 * A one-sided version of this trope is used for laughs in Ranma ½. Doctor Tofu is a licensed chiropractor who has been practicing as a professional at least since Akane was in primary school (and who may be over 100 years old, if one takes a certain comment seriously). He is also desperately in love with Kasumi Tendo, a 19 year old girl, and has been since she was in Junior High herself. Kasumi isn't aware of this, 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. Akane, meanwhile, begins the series with a deep crush on Tofu that she's been sporting since she was about five years old... though she gets over him shortly into the series' run, considering him more as her Big Brother Mentor from then on. 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 again later on when Ranma eats a Love Pill and falls for Cologne, one of the oldest characters in the series.


 * In fact, Rumiko Takahashi seems to dislike this trope. Though it is invoked in Maison Ikkoku, where Kyoko's husband Soichirou was also her teacher at high school, the man 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. Meanwhile, in Inuyasha, she tried as hard as she could to sink the Fan-Preferred Couple of Sesshomaru and Rin, mostly by the Koharu incident where the characters reacted to Miroku proposing to Koharu with shock and disgust and also by turning Rin into a Shipper on Deck for Sesshomaru/Kagura. For those unfamiliar with the series, Sesshomaru is a Really 700 Years Old dog-demon who, Draco in Leather Pants aside, is one of the coldest and most ruthless characters in the series and avoids being a major villain in the early part of the series only because he's really too apathetic. Rin, on the other hand, is a human girl who is barely prepubescent, and the source of Sesshomaru grudgingly realising humans aren't entirely insignificant.
 * Well, considering that the series' alpha couple are a teenage human girl and a half demon who was probably at least 30 even before his decades-long forced nap, her protests fall a bit flat. Sorry, Ms. Takahashi...
 * Subverted in that demons age much slower than humans, so Inuyahsa is, at his age, an adolescent just like Kagome.
 * If we're going to go that route, we might as well note that Sesshoumaru, as a full demon, would age even more slowly, and is supposed to be roughly the equivalent of nineteen, which almostnotreally manages to de-squick the relationship so many fans imagine between himself and Rin.
 * Still not the same since then it becomes Wife Husbandry, which is not the case with Inuyasha and Kagome.
 * Mahou Sensei Negima also has a one-sided version involving Asuna's (15) attraction to Takamichi (mid 30s). Another one-sided example would be Evangeline for Nagi, which is sort of funny considering the apparent ages of the two.
 * Konoka expresses discontent at her Grandfather trying to set her up in one of these in an arranged marriage, with some of the potential partners being twice her age. She's 15.
 * Though they never met in the main story, this is implied to have happened between
 * 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 . 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.
 * The Official Couple of the Girls Love Manga Creo the Crimson Crises is the main character, a teenage schoolgirl and a demon woman who's at least in her mid twenties.
 * 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.
 * In Code Geass, it's implied that 13-year-old Tianzi and 24-year-old Xingke are in love with each other, and 15-year-old Anya & in-his-late-20s Jeremiah have somehow ended up together on their own orange farm (though the last one can be seen also as a sibling or adoptive father/daughter relationship).
 * Most fans prefer to think that Jeremiah hooked up with Ninja Maid Sayoko (who's in a similar age bracket) and then they adopted Anya.
 * As for Tianzi and Xingke, Kaguya ships them.
 * Tianzi and Xingke's relationship doesn't seem quite as odd because she was previously engaged to the prince Odysseus eu Britannia, who is probably in his thirties due to his being older than his twenty-seven-year-old brother Schneizel el Britannia. Values Dissonance ahoy: in the past centuries, such hook-ups were seen as normal among noblemen.
 * While the nine year difference between Sakaguchi Alice and Kobayashi Rin of Please Save My Earth may not, relatively, seem like a lot, it's much weirder when you consider that Rin was seven when he asked to be engaged to the 16-year-old Alice.
 * In RahXephon, Haruka Shitow, who is about thirty, seems to have romantic interest in Ayato Kamina, who is seventeen..
 * 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.
 * Allen Schezar (age 21) of Vision of Escaflowne finds himself in the center of a Love Triangle between Hitomi and Millerna, both of whom are only 15. If you suspect that Allen's thing for barely legal Ingenues might be a case of misdirected paternal/BigBrotherInstinct due to his past, You'd be right.
 * Meisuke "Nube" Nueno from Hell Teacher Nube finds himself in the receiving end of Yukime's affections. He then invokes this trope to try push her away, since he's 25 years old and she's 16.
 * Arguably in Magic Knight Rayearth with Hikaru, Eagle and Lantis. Their exact ages are unknown (especially since the possibility of long life exists) but they're easily young adult men in their early to mid 20's. Hikaru is a 14 year old Middle Schooler.
 * Itsuki "Ikki" Minami, the 15-year old protagonist of Air Gear developed a crush on 20-something Simca pretty much the moment he first saw her. Simca, in turn, has reciprocated... sort of. It's an on-and-off thing.
 * 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.
 * Also used for . Also probably applies for.
 * Also.
 * The main two characters of Godannar are a Anna and Goh, a 17 year-old girl still finishing school and a 29 year-old Super Robot pilot. Once more, Anna fell in love with him after he saved her life when she was 12. Lampshaded in the first episode, when Anna's mother/Go's old friend Kiriko jokingly mentions that maybe she should have made a move on Goh since they've been working together (at 35, she's 6 years closer to Goh's age than Anna). Not to mention, this is treated somewhat more realistically, since the age difference does bring up more than one problem between the two: Go used to be in love with his dead partner Millia, and Anna is extremely insecure in regards to their relationship.
 * This is one of the very few shows to undo this trope without breaking up the couple in question. In the finale,
 * Soubi of Loveless is 20 years old but more or less has the hots for the 12-year-old Ritsuka.
 * Van Hohenheim and Trisha Elric of Fullmetal Alchemist. Even if you factor out, 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.
 * In Death Note, Chief Soichiro Yagami is revealed to be 7 years older than his wife, Sachiko. Despite the tragedy that befalls the Yagami family, they are portrayed to have an otherwise normal, loving relationship with each other.
 * Junjou Romantica loves this. While the Egoist couple may only have four years between them (and they angst plenty about that), the Romantica couple is ten years apart. And last but not least is the Terrorist duo—17 years apart, not to mention one is in high school and the other is a college professor. But it gets worse—the student also happens to be the younger brother of the professor's ex-wife. And his boss' son.
 * 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
 * Another short story has what appears to be this between an older man and a younger woman...
 * Anzu's parents in Hanamaru Kindergarten. Her mother was a high school student when she married her art teacher, who was in his twenties at the time of marriage.
 * 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.
 * and  are this at the tail end of Tokyo Crazy Paradise.
 * 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 Detective Conan, Inspector Juzo Megure and his wife Midori are also a May September deal. They met when she was in highschool and he was already a junior officer, meaning he was in his early-mid 20's.
 * More than one case also features marriages/relationships like this.. but one of the spouses is likely to be injured or dead. The writer Daisuke Torakura married a woman named Etsuko who was 20 years younger than him ; he hires Kogoro to keep an eye on Etsuko since she's cheating on him...  Another case has the famous actor Kouzaburou Hijikata (mid 50's) and his wife and fellow actress Isami (mid to late 30's),  ; and then there's the lawyer Shouhei Tatsumi (48) and his wife Kazumi (30),
 * Ristorante Paradiso has the main couple, Nicoletta (early 20's) and Claudio (mid 40's), as well as Vito and Marina.
 * In Chrono Crusade, 16-year-old Rosette is sweet on er Parental Substitute Father Remington, who publicly claims to be 27 . 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.
 * Kimi wa Petto has a gender-inverted version between its main characters with Sumire being 12 years older than Momo/Takeshi.
 * In Digimon Adventure 02's Japanese version (and the dubs that follow it, like the Latin-American one), when Iori questions Miyako's crush on Ken since she's a year older than him, Miyako reveals that her mother is five years older than her father so she sees no problem with such hook-ups.
 * 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.
 * Genderflipped in Kaoru Mori's A Bride's Story aka Otoyomegatari, where the bride Amir is a 20-year-old female Country Mouse and her arranged husband Karluk is a 12-year-old Cute Shotaro Boy.
 * 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 My-HiME, who is 24 (although she tries to convince others that she's 17), is romantically interested in her professor, who is in his mid-fifties.
 * While their relationship would in reality be a a different version of this, Holo and Lawrence would be this if the former was mortal: She has a human form of a girl in her mid-teens, and he's a traveling merchant who can't be less than his mid-twenties, and may in fact be in his early or mid-thirties.
 * Let us not forget Kenshin and Kaoru of Rurouni Kenshin, she's 17, he's 28. Though he at least is Older Than They Look.
 * Similarly, 16-year-old Misao has strong feelings for 27-year-old Aoshi.
 * The ending of Kobato. has
 * A May-December romance is revealed in the final moments of the "Where Are They Now?" epilogue of Nadia: The Secret of Blue Water, when we learn that the Narrator is a late-teens Marie who is now involved with Sanson. Marie was four years old throughout most of the series and Sanson was 27.  However Squicky as that may seem now, Nadia takes place in the Victorian era, and as the Real Life section below mentions, this would have been a desirable age difference at that time.
 * A May-December romance is revealed in the final moments of the "Where Are They Now?" epilogue of Nadia: The Secret of Blue Water, when we learn that the Narrator is a late-teens Marie who is now involved with Sanson. Marie was four years old throughout most of the series and Sanson was 27.  However Squicky as that may seem now, Nadia takes place in the Victorian era, and as the Real Life section below mentions, this would have been a desirable age difference at that time.

Comic Books

 * While their age difference was not outright stated due to Comic Book Time, DC Comics' Barbara Gordon (Oracle) is canonically older than her on-again/off-again love interest Dick Grayson (Nightwing).
 * At one point pre-Crisis, she was a Congresswoman while he was a college student. At the very least, canonically, she was a college graduate when he was sixteen or so.
 * 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.
 * Rather standard in the Marvel Universe, especially during the Silver Age. In contrast to DC heroes, the older male heroes actually married their younger female sidekicks/students when they came of age. Most notable examples are Reed Richards and Susan Storm, Hank Pym and Janet Van Dyne, Stephen Strange and Clea, and Brian Braddock and Meggan.
 * In the dystopian divergent timeline of 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.
 * 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. Occasionally it verges into May–September or Mayfly-December Romance territory as characters are rejuvenated through comic book-science means or have powers that render them impervious to the effects of aging. Thus Magneto in the main timeline has the body of a man in his 30s since being de-aged and partially re-aged, which takes some of the sting out of his relationships with Cyclops' ex-girlfriend Lee Forrester and with Rogue. 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.
 * Reed Richards and Susan Storm are a May September example. They met when he was 19 and she was 12-13, she fell for him at the moment, but thankfully they started dating only when they both were Older and Wiser.
 * This happens to Sue Storm a lot; she's also 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.)
 * In Top Ten 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.
 * Played with in Ultimate Spider-Man. Spider-Man is presented as a teenager, while Black Cat is shown as an adult. She kisses him a few times, then actually takes off his mask and finds that there's a teenager under there. Her response? Vomiting.
 * Played for Squick in "The Judas Contract" storyline from New Teen Titans in the 1980s. Forty-plus Deathstroke the Terminator had an implicitly sexual relationship with fifteen-year-old psychotic Terra. Also shades of Mayfly-December Romance, as Deathstroke is apparently immortal.
 * Done in both directions for Green Lantern Hal Jordan. At some point in his thirties or forties he had a relationship with thirteen-year-old Green-Skinned Space Babe Arisia. This was inverted when an Author's Saving Throw revealed that thirteen years on her home planet is something like two hundred and forty on Earth.
 * Watchmen: Fifty(?)-year-old Dr. Manhattan and sixteen-year-old Silk Spectre II (to the fury of Janey, Manhattan's long-time girlfriend), although it can be argued that Manhattan is "only" around thirty since he "died", putting him roughly the same age as Spectre II's lover Nite Owl II; either way, still rather squicky.
 * A flashback in Alpha Flight showed that when Heather MacNeil first told her eventual husband, James Hudson, that she loved him, his reaction was that she was far too young. He said, "I could probably get arrested just for being in the same room with you with the door closed!" (approximate quote).
 * 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.

Fairy Tales and Folklore
"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."
 * 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.

Fan Works

 * Popular in Naruto fan fiction. The title character is paired with Anko (who is at least ten years his senior) in a number of the more well-known/serious stories, including one of the more popular stories irght now, That Look, by lord of land of fire.
 * Also popular seems to be pairing Naruto with Kurenai, Mei, and Tsunade.
 * Hell, Naruto fan fictions are a treasure trove for these. Sakura and Shikamaru are often paired up with Kakashi and Kurenai despite being thirteen years younger than them, Sasori (35) is sixteen years older than Deidara (19), and Kakuzu, who is 91, is paired up with Hidan, who is 22. And lets not get started on Orochimaru.
 * 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 fanfiction, Severus Snape/Hermione Granger. Sometimes the age difference is circumvented by way of clever use of the Time-Turner from Prisoner of Azkaban.
 * Just Snape and Hermione? He's paired with Harry and Draco as often, and there are small bands of fans into similar gap relationships.
 * For a more subtle version, Dumbledore/McGonagall. They both qualify as "old" now, but Word of God says she's seventy while he seems to be somewhere between 120 and 150. Either way, Fridge Logic says he would have already been her elderly teacher when she first passed through the doors of Hogwarts.
 * Stray is either a May/December or May/September romance, depending on whether you look at birth date or years of lived experience (there's Time Travel involved.) Adamska was born in 1944 and is twenty, Hal was born in the early to mid 1970s and is in his thirties.
 * Tin Man - both Glitch and Cain are in their late 30s or early 40s, and DG is explicitly said to be 20.
 * Any Yami no Matsuei fic that ships Tsuzuki/Hisoka. Their physical ages (being Shinigami, their bodies don't age) are 26 and 17 respectively. 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.
 * The most popular pairing in the Beyond Good and Evil fandom is Jade/Double H, which would be an age difference of about 15–16 years. However, some people also like paring Jade with Pey'j--which has hints of Parental Incest to go with its much larger age gap.
 * Razputin from Psychonauts has been paired with both of his camp counselors, Sasha and Milla—sometimes aged-up, but sometimes not. He's ten years old to start with; Sasha and Milla's ages are not stated, but given the amount of history they have, they could easily be in their early to mid 30's.
 * One faction of the Professor Layton fandom is quite fond of pairing the eponymous professor with his young assistant Luke. Luke is 13, the Professor 37. Others like to pair him with his surrogate daughter Flora, who is approximately 16.
 * Final Fantasy VII has the pairing of Yuffie and Vincent. They have no official ages, but she's a teenager, and he's been asleep in that coffin for some time.
 * Actually, as of DoC, Vincent is 60, and Yuffie is 19. Less squicky in the fact that Vincent has the emotional capacity of an Emo teenager and is physically stuck at 27.
 * Neon Genesis Evangelion fan fiction authors have fully embraced this trope, especially with Shinji, who gets paired with everyone, including his own guardian Misato Katsuragi (about fifteen years older the fourteen year old in question). Fanfic authors have also occasionally stated that the Yui Ikari/Kozo Fuyutsuki relationship was not platonic.
 * Touhou fandom has the Rinnosuke/Marisa pairing. Marisa is a (relatively) normal human while Rinnosuke, although not effectively immortal as with other youkai (he is a half-youkai apparently, however that works), ages far slower than humans and appeared fairly identical when Marisa was a child.
 * In Axis Powers Hetalia, considering that America and England are countries, England has been around a lot longer than America, even raising America as an older brother. (Somewhat softened by how their human ages of sorts are relatively close: America is the equivalent of a 19-year-old, while England is the equivalent of a man in his early-to-mid 20's)
 * In fact, plenty of pairings involving China and Turkey, both seen interacting with their potential love interests, Japan and Greece, who are a lot younger than them. Keep in mind there were strips where they were children while neither China or Turkey aged a day since then. Heck, even Japan and Greece might fall under this, considering that Japan is probably at least two thousand years old and Greece is shown as a child during Ottoman rule (sometime in the 1500s, probably hitting his growth spurt around the Greek Independence Wars), although most Greece/Japan fan works depict Greece as more mature than many other nations older than him. (And Greece also grew very fast by nation-tan standards, considering that he's said to look like he's in his late 20's now—pretty impressive, considering that he's still a kid around the Chibitalia years, but Italy looks much younger than Greece now.)
 * The most recent example would be Turkey and either Iceland or Hungary. On one hand Iceland is the youngest of the Nordic group (he's said to look like a 17-year-old at most), whereas Turkey is physically old enough to have Iceland refer to him as "mister" (looking at very least like a man in his late 30's/maybe early 40's). On the other, while Hungary does look older than Iceland (at least in her early-mid 20's in looks), she has been fighting Turkey since she was a little girl and he was already a full-grown adult as well as the Ottoman Empire.
 * When Japan and China are paired up with the other Asians, this trope is also invoked frequently. Specially in the case of either of them with Taiwan, which may even reach Wife Husbandry extremes since she has the looks of a 15 year old girl, and Fanon dictates that she was raised by Japan at some point (to reflect the Japanese occupation of Taiwan.)
 * There's also France who's often paired up with Canada or Seychelles (and once or twice, Vietnam), nations he raised as his kid colonies. France is said to have the looks of a man in his mid to late 20's, while the other three look like in their late teens.
 * And Romano with either Spain or Belgium, too. In the days when Romano and Belgium were Spain's colonies, Spain was the eldest of the group while Belgium was a teenager and Romano was a child. (While Belgium's brother Netherlands looks considerably older than them both, likely a little younger than Spain himself.)
 * This appears to be the case in the 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 as of this fic) and Iroh (70 as of this fic).
 * The incredibly sad 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!
 * Most Doctor/Companion pairings for Doctor Who are Mayfly-December Romance, but during Rose Tyler's time on the show, Mickey Smith (early 20s)/Jackie Tyler (around 40) was a popular Ship Mate to Ninth or Tenth Doctor/Rose in fanfiction. Less common now that  are canon.
 * The Lord of the Rings fanfic The Roots of the Ivy, which features Merry/Eowyn pairing (he is much older than her, even for a hobbit). Though their main problem definitely is not his age. Mostly canon up to the end of the books, then not so much. Though age difference becomes a huge problem later for.
 * In Hunting the Unicorn, Blaine has a very distinct pattern of pursuing (or being pursued by) someone at least a couple of years older than him.
 * In the Teen Titans Fanfic Requiem for Methuselah Garfield Logan (Beast Boy) is immortal instead of a shape shifter and has a Romance with Raven who is 20, but is very depressed that he couldn't have a May–December Romance with any of his previous wives because they would leave him once they discovered he was immortal.
 * The Nothing But Time series of Homestuck fanfics focuses on the relationship between John and Dave. Considering John's own son in the fic is slightly older than Dave, the age gap between the two is pretty large.
 * Team Fortress 2: Some of the pairings involving the Medic can be this, such as pairing him with the Scout or Miss Pauling.

Film

 * 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.
 * Labyrinth has the goblin king, Jareth, fall in love with teenager Sarah Williams. It becomes even weirder when you realize that he's fey and thus could be centuries old.
 * Let's not forget that David Bowie, the actor who played Jareth, was in his late thirties, early forties; while Jennifer Connelly, Sarah, was fifteen going on sixteen.
 * Les Dimanches de Ville-d'Avray (Sundays and Cybèle). Thirty-year-old Pierre has a chaste but definitely romantic relationship with eleven-year-old Cybèle, who says she'll marry him when she's eighteen. Pierre is amnesic and therefore quite childlike himself, and he's also got a profound unconscious trauma from maybe having killed a little girl as a fighter pilot.
 * In La Puce, a 14-year-old girl meets an older man at the beach. He's attracted to her; she's not in love with him, but she decides to lose her virginity to him, and goes through with it.
 * In Beau-père, a 29-year-old man lives with his girlfriend and with her 14-year-old daughter, whom he's been helping to raise for the past 8 years. The girlfriend and mother is killed in a car crash and the (ex officio) stepdaughter asks to stay with her stepdad instead of going to live with her biological dad. Soon she discovers that she is attracted to her stepdad, and she persistently makes advances to him; he's tempted, but refuses, then eventually gives in.
 * In Louis Malle's Pretty Baby, a 12-year-old girl, Violet, is growing up in a New Orleans brothel at the turn of the 20th century. She has her virginity auctioned off to a rich man. Then a young photographer comes to the brothel to photograph the women. Violet crushes on him, he falls in love with her, and they marry,
 * I Start Counting. A girl of 14, going on 15, has been raised by an adoptive family all her life. Recently she has fallen in love with her 32-year-old adopted brother. She dreams of marrying him when she is old enough, which in the UK means 16. Her best friend, a girl the same age, flirts with some older guys.
 * Broken Blossoms, in which a man falls in love with a 15-year-old girl in need of his protection, but refrains even from kissing her, since she doesn't seem keen on the idea.
 * L'Effrontée. A girl of 13, going on 14, meets a young man in the Merchant Marine. He initially thinks she is 14; she tells him she's 15. She's fine with a peck on the lips and a movie date, but things turn very nasty: he tries to rape her and she has to smash a glass globe over his head to escape.
 * In the short film À mains nues, a 12-year-old girl is growing breasts and feels envious of her best friend's new boyfriend. She meets a grown young man who knew her when she was younger and who comments on how 'grown-up' she's looking, and how she's too old for them to wrestle now. He ends up giving her her first kiss, about which she has confused feelings.
 * 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.
 * Two in the 1972 sexploitation flick Night Child (AKA Night Hair Child and What the Peeper Saw). A rich 42-year-old man, his wife only two years dead, marries a 22-year-old woman. They have plenty of sex but don't seem to love each other. The man's 12-year-old son turns out to be a murderer. He also turns out to be a voyeur. And to top everything off there is a certain sexual charge between the son and the new wife. No sooner has he met her than he grabs her breasts. At one point he makes her strip for him in exchange for information she wants. While sedated, she dreams that they are kissing naked in bed while the husband/father looks on smiling. At another, they actually do kiss and he suggests they kill off the husband/father and become lovers, but a plot twist nixes that suggestion.
 * In the first Legally Blonde movie,
 * Lost in Translation. Charlotte (Scarlett Johansson) is in her 20s. Bob (Bill Murray) is in his is mid-to-late 50s. Made even more crazy when you consider that Johansson was only 18 during filming. Completely justified in the story, as Bob is suffering a midlife crisis, and Charlotte is having trouble in her recent marriage. One of the more heartwarming examples out there.
 * Dr. Grant and Dr. Sattler from Jurassic Park, although they're a bit wish-washy about their relationship.
 * All the Poison Ivy films are made of this.
 * How Stella Got Her Groove Back. Based on the book, based on the Real Life of the author. IRL, it didn't end happily.
 * The Graduate contains the trope-naming character Mrs. Robinson, who seduces the titular college graduate, Ben Braddock. She mentions being twice his age, and her daughter is only slightly younger than he is.
 * In Bill and Teds Excellent Adventure, Bill's stepmother Missy is only three years older than he is. In Bill and Teds Bogus Journey, she's now Ted's stepmother, having switched husbands between movies (and Ted's father appears to be even older than Bill's).
 * A large number of James Bond films; Goldfinger and On Her Majesty's Secret Service are the only films when the Bond Girl is older than 007 himself.
 * During the filming of A View to a Kill, Roger Moore discovered that he was older than Tanya Roberts' mother.
 * Quentin Tarantino's Kill Bill: Bill with the Bride, Elle Driver, and most likely Sophie as well.
 * It's worth noting that when Bill shows up to the Bride's wedding, she tells 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.)
 * In Sin City, John Hartigan is nearly sixty while Nancy is only nineteen - which is part of what makes him uncomfortable about pursuing a relationship with her despite the mutual interest.
 * 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.)
 * Spirited Away has the schoolgirl Chihiro falling in love with a river spirit who appears a good bit older than her and is actually probably a lot older.
 * Happens in Eat Drink Man Woman between 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. Then again, the Chairman is played by Ken Watanabe ...
 * Aragorn and Arwen, in The Lord of the Rings. By millennia. It causes some tension . Also, Aragorn and Eowyn, but only by a few decades. Less tension, which is.
 * Although they all took to be near the same age as each other, Aragon is actually about twice as old as he looks, and Arwen is immortal and may be hundreds or thousands of years old.
 * They are also very distant cousins, due to Aragon being a direct descendant of Elendill, who was himself a descendant of Elros. Elros was the brother of Elrond and also half-elven. he was given the choice to live as an Elf or a Man and chose the latter,
 * 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 Rochefort (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.
 * Tom Greer (Bruce Willis) and Maggie Greer (Rosamund Pike) in Surrogates.
 * The Rebound has divorcee Sandy and her nanny Aram falling for each other. He's 15 years younger than her. A rare gender-swapped version of this trope.
 * Bloomington has a lesbian version between a psychology professor and her student.
 * 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 Jürgen Prochnow) and Damiana (played by Blanca Jara who was 23 at the time).
 * While this appears to be the case in RED, the actors playing them are much closer in age than their characters.
 * Perhaps not intentional on the director's part, but the actors playing Sang-hyun and Tae-ju in Thirst are twenty years apart.

Literature
"Boy Blue: Oh, I see. Six-year-old little girls aren't likely to look at three-year-old little boys that way, aren't they? Christobel: No, Boy Blue, it wasn't that way. When you were six, I was sixteen."
 * 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).
 * Jane Eyre is just 18. Rochester is in his late thirties.
 * A servant comments, "Mr Rochester was forty, and the governess not twenty, and when men of his age fall in love with girls, they are often as if they had been bewitched."
 * Little Dorrit. Arthur Clennam and Amy Dorrit . Arthur is about twenty years older than Amy.
 * In Little Women, 25-year-old Jo hooks up with 40-year-old Professor Bhaer. A possible May September hook-up is the one between 17-year-old Meg and 25-year-old John Brooke.
 * Francis Thompson wrote poems about the young girls he fell in love with, including The Poppy: To Monica, which broods on the inherent difficulties of an adult's being in love with a child. "You know not love from amity / Nor my reported self from me ... I am but, my sweet, your foster-lover / Knowing well that when certain years are over / You vanish from me to another -- / Yet I know, and I love, like the foster-mother."
 * Ernest Dowson wrote poem after poem about his unrequited love for Adelaide 'Missie' Foltinowicz.
 * In Mary Renault's Return to Night, a 35-year-old woman doctor has a relationship with a man 11 years younger, who has been a patient of hers. In Renault's North Face, a man of about 40 and a woman of 25 get together.
 * Lolita, if you believe Humbert Humbert's version of events.
 * In the novel Les Dimanches de Ville-d'Avray, a 28-year-old former criminal, amnesic and childlike after an accident, lives with an adult female prostitute, who loves him, but he also forms a romantic friendship with a 10-year-old girl whose father has left her at an orphanage. The book was turned into a film with the ages of the pair raised to 30 and 11.
 * As the protagonist of Robert A. Heinlein's novel I Will Fear No Evil has the brain of a 90-year-old man and the body of a 20-year-old woman, most of his/her relationships are arguably May-December Romances in both directions.
 * Also many relationships among Howard Families members, where spouses can differ in age by centuries. One of the most heartwarming and tear-jerking is the Mayfly-December Romance between Lazarus Long and Dora, in Time Enough for Love.
 * Robin McKinley (who appears to have a bit of Author Appeal for this trope) wrote Beauty, a retelling of Beauty and The Beast. In it, every female character who marries ends up with a man at least a decade older than her. The largest gaps are twenty-three years between Beauty's parents, and her own relationship with Beast has a technical gap of over two hundred years, and a physical/practical gap of twenty. Justified in that the era in which the book takes place would have encouraged this trope, though Beast does apologize for being quite a bit older than Beauty even in his human form.
 * In her Sleeping Beauty retelling, Spindle's End, we get Rosie, who we watch grow up from an infant to a 20-year-old over the course of the book, and, who has to be at least 25 years older than her, considering he was already an adult living in the town when Rosie arrived as an infant. Somewhat justified in that he's , but still.
 * The Reader (Der Vorleser) has a 16 year old boy hook up with a mid thirties to 40 year old woman.
 * Daine and eventual romance in the The Immortals books. (He's twice her age.)
 * Tamora Pierce likes this trope. There's also a significant gap (although not as big as the one mentioned above) between Alanna and.
 * Also Aly and Nawat. It's easy to forget since he looks about nineteen or twenty to Aly's seventeen, but he's actually three. And a transformed crow.
 * In Florence Barclay's novel Through the Postern Gate, Guy of Chelsea aka Boy Blue Likes Older Women and is a Keet who pursues Hot Librarian Ojou Christobel Charteris, who is ten years older than he is and has known him since he was a child and she was a teenager. In fact, one of the reasons why Christobel hesitates to accept Boy's advances is because of their age difference, as well as a possible marriage proposal from the local Professor. Paraphrased:


 * In the O. Henry short story "October and June", 28-year-old Theodora tells The Captain they can't be together because of their age difference.
 * 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
 * While strictly speaking a Mayfly-December Romance, the feeling of this trope is impossible to avoid in Bujold's The Sharing Knife books, 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. The fact that they both expect to last 50-60 more years barring violence or illness and die about the same time is of little comfort even without the Fantastic Racism in the mix.
 * Bujold seems to have a thing for her male characters marrying younger women, with Miles being the exception. Aral Vorkosigan is a decade older than Cordelia, and Lupe dy Cazaril, the protagonist of The Curse of Chalion, is 35 (but looks older) to Beatriz's 19.
 * In the Kushiel's Legacy series, Father figure Delaunay in his late thirties at this point is put into a romantic relationship with his adoptive son/student Alcuin a boy around 16 tops at this point. (Admittedly it was Alcuin who started it.)
 * Dr. Strong and his much, much younger wife Anne in Charles Dickens' David Copperfield.
 * 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;
 * 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 and, although  is decades older.
 * The Star Trek Expanded Universe marries Spock off to the much younger.
 * All over the place in Honorverse, due to Prolong treatments that extend human life to 250–300 years range and significantly slow or even stop the aging process, depending on the technology generation. Honor herself, third and latest generation recipient, is 62 as of the latest novel, and just barely stopped looking like a teenager. Her husband,, is 100 (yep, that's one hundred years old), and being the first-gen prolong recipient looks barely 40.
 * 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). And his daughter  chooses a teenager to marry when she is six. Also the case with Polgara and Durnik in the Belgariad/Mallorean series, although   keeps it from being a Mayfly-December Romance.
 * The Mary Russell mysteries by Laurie R. King feature a young woman who marries Sherlock Holmes—who is well over the age of sixty.
 * 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.
 * In The Paladin by C. J. Cherryh, exiled Samurai-type Master Swordsman Shoka, about 40, and his peasant girl student Taizu, in her late teens, grow to love each other.
 * In Twilight, Claire and Quil. Quil is in his teens and Claire is a toddler. The actual difference is something like fourteen years, but she's a freaking child!
 * Forget that. Jacob, seventeen, is paired up with Renesmee when she's an infant. At least she has Plot-Relevant Age-Up.
 * I think you people are forgetting the main romance in the series: Bella, 17-18, is paired with Edward, who is in his hundreds. . It's a good thing he's hot, otherwise he'd be a pedophile!
 * Amara and Bernard in the Codex Alera. How it manages to be cute instead of squicky is unknown, but it works.
 * There's also the relationship between Aldrick ex Gladius and Odiana; when they met, he was roughly in his late twenties/early thirties, while she was in her middle teens. To add to the discomfort of it all, Odiana had recently been freed from being a sexual slave for a group of slavers by Aldrick and his fellows, and she'd been deeply disturbed and near-insane until Aldrick, erm, calmed her down.
 * In the Inheritance Cycle, Eragon is only around 16, while Arya is over one hundred. Although, Arya doesn't seem interested in Eragon, Eragon doesn't seem to care about the age difference! Granted he will be near immortal now that he's a dragon-rider, but she is still around 85 years older than him!
 * Which she and other characters frequently remind him. He's just blinded by teenage hormones.
 * Xanth has many relationships formed over the course of its more than 30 books), and some of these include May December Romances, such as the case the prince Naldo Naga and Mela Merwoman, the latter being 11 years his senior. Some relationships, however, involve demons, nearly all of which have arbitrarily long life-spans and are never clearly defined. What truly clenches a May December Romance here however, and may extend into more a Hadean-one-minute-ago Romance are when the capital-D Demons get involved, the Demons that existed since the dawn of time and embody universal forces. At least three of these of formed with mortals over its run, 2 of which in book #33.
 * And to further stretch it out? The first two involved humans and Demons. The third involved a spider and a Demon. Yes, an ordinary, dies-in-a-year spider.
 * In the Heralds of Valdemar, Vanyel falls in love with his classmate, Tylendel. They are both in their late teens, and eventually realize that they have a rare lifebond. Tylendel dies. Vanyel is heartbroken. Fast forward, and now the forty-year-old Vanyel meets the twenty-year-old Stefen. Stefen has a huge crush on Vanyel and eventually persuades him to ignore public opinion and give their relationship a chance. Then they have a lifebond with each other, supposedly a once-in-a-lifetime occurrence. Eventually it turns out that
 * Lackey likes this trope: Dirk (mid-thirties) marries Talia (just barely twenty). Same age difference for Keren and Sherrill.
 * Aleksandr Griboyedov and Nino Chavchavadze in The Death of the Vazir Mukhtar. By the time of the book he is 34 and she is 16, but he has been longing after her even before. They get married in the middle of the second half of the book...
 * Jane Austen's Sense and Sensibility: Colonel Brandon is 19 years older than Marianne Dashwood. This was not considered at all squicky at the time, however, and is treated as more of a Beast and Beauty obstacle in the novel, with Marianne needing to look past the surface and see that the regard of a selfless, honest man is more valuable than attraction to a dashing, young but unreliable Casanova. Hidden Depths are a running theme in Jane Austen novels.
 * Emma: Mr. Knightley is 16 years older than Emma Woodhouse (the sister of his brother's wife) and has held a fatherly role in her life for years, scolding her for inappropriate behavior.
 * Richelle Mead's Vampire Academy series has several May/September examples. Dimitri Belikov is seven years older than 17-year-old lead Rose Hathaway—which is a big deal because she's his student. Dimitri's other love interest, Tasha Ozera, is said to be about seven years older than he is, too. There's also a significant age gap between Rose's biological parents—her mom was twenty when she was born, and her father is implied to have been a decade or more older.
 * In Girl Overboard by Justina Chen Headley, the main character Syrah's parents are very far apart in age; her mother is in her 40s and her dad is 70.
 * In Robert Jordan's 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.
 * In Vernor Vinge's A Deepness in The Sky, the Big Bad has a Human Popsicle as his girlfriend. The hero has the Human Popsicle as his little sister like childhood friend, separates from his own girlfriend and marries the Human Popsicle instead.
 * Nick Charles in Dashiell Hammett's The Thin Man is forty-one; his wife Nora is twenty-six. Oh, and based on one comment Nick makes, he married her seven years ago—when she was nineteen.
 * That's nothing (esp. since both are older when they actually marry). Scarlett's parents Ellen and Gerald were fifteen / early forties respectively.
 * Sharon Nichols and Badass Spaniard Ruy Sanchez de Casador y Ortiz in 1632. Sharon is in her early to mid-twenties, while Ruy is somewhere around his mid-fifties.
 * In James H. Schmitz's The Witches of Karres, young witch Goth (nine or ten) informs Captain Pausert (twenty-eight) she's going to marry him when she grows up. The Captain later explains to Goth's father that while he's fond of her, he has no intention of taking her seriously. Goth's father indulgently replies that he didn't take his wife seriously, either.
 * In Memoirs of a Geisha, Sayuri is in love with the Chairman, who is twenty-eight years older than her.
 * Quiet a few of relationships between humans and vampires in The Vampire Chronicles, notably the relationship between Armand (15 at the time) and Marius (40 when he was turned into a vampire, as a vampire he at least a thousand years old) in The Vampire Armand. A source of Squick for many fans, though mostly due to the more than slightly pedophiliac nature of the relationship.
 * One short story, name forgotten, involves a female college student telling her father that she's planning on marrying her professor, who is older than her father and has children from a previous marriage older than she is. The father makes jokes about his daughter collecting Social Security benefits before he does.
 * Troubleshooters has several of these, though unusually the 'December' is often the woman. Molly and Jones, Joan and Mike (a seven year difference only, but she's very bothered by it), Meg and John (another smaller age difference, but she's very bothered by it; a Double Standard in that she's not bothered by her husband  being about fifteen years older than her). Also Gina and Max; Max is over twenty years older than her.
 * In the American Girls Collection the popular ships of Josefina/Patrick (16/22 if the writer ups their ages for a fanfic), Felicity/Ben and Kit/Will factor in as May December Romance pairings, especially so with the Felicity and Josefina pairings, whose men the shippers pair them with are often separated by at least six years, though Kit/Will only has five.
 * In Hilary McKay's Casson Family Series as of Rose's blog at her official site, the popular fandom ship of Tom Levin and Permanent Rose Casson has established that Rose is now fourteen and Tom eighteen,and Rose has wrote the blog as a result of her brother, Indigo, trying to dissuade her from loving Tom, who is five years older than her, which makes her extremely unhappy, and so she later writes the blog to help her get over it - though Rose has never really gotten over Tom Levin. Indigo/Sarah to lesser extent, though in this case Sarah is the older one by two years.
 * In Anne McCaffrey's Damia, the title character winds up with a man who was at least 20 years old when she was born (And he's known her since birth too!).
 * Hannibal Lecter and Clarice Starling from the Silence of the Lambs series. He's thirty years older than her.
 * 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."
 * Sort of justified insofar as.
 * From Tales of the Frog Princess: Prince Garrid and Li'l. Garrid's a vampire, Li'l's a normal bat. This means that she is probably around five in human years, while Garrid is at least 500.
 * In The Count of Monte Cristo, the Count's ward Haydee is in love with him. Eventually, after he has taken revenge on all who wronged him (and become disillusioned with revenge after a child died because of his schemes), she confesses her feelings. Seeing this as a new reason to live, the Count reciprocates her love.
 * 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. There's also the romance between Brutus and Alexandria; the age difference there isn't as great, but Alexandria has enough of a bosom to distract Marcus and Gaius when the boys are both 10 years old.
 * 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 Duke’s palace, pretends to be in love with Don Quixote, a 50 year old man. He stoically supports her teasing and mean pranks because he believes she’s in love with him because he is a knight, but he never attempts anything because he wants to be loyal to his (imaginary) lover Dulcinea and is very happy when he abandons her and the palace. Being an honest man, he confesses to Sancho that Altisidora’s feelings caused him more confusion than pity, showing us how awkward and foolish would be this kind of relationship in Real Life.
 * 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.
 * 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.

Live Action TV
"Monica:"You're not a senior?" Guy Of The Week: "Oh, I'm a senior. Just not a college senior...""
 * All in The Family/Archie Bunker's Place: A Season 9 episode of "Family" saw Archie's brother, Fred (who is in his mid-50s), marry an 18-year-old girl. During the last two seasons of Archie Bunker's Place, Archie's 18-year-old niece Billie (Denise Miller) begins an on-again/off-again relationship with Archie's business partner, 33-year-old Gary Raboneaux (Barry Gordon).
 * Friends had a May–September version, where Phoebe's 18-year-old brother married a 44-year-old woman. (His Home Ec teacher, in fact.)
 * In the episode "The One With Joey's New Brain", Joey got involved with an actress on his show who was at least 20 years older than him.
 * In the episode "The One With The Rumor", it was revealed that Ross made out with his librarian in high school, she was 33 years older than him.
 * Also used as a one-off gag a couple of times: Rachel dated a younger guy to make Ross jealous (Ross: "He's just using you to get into R-rated movies"), and Monica dated a younger guy who eventually admitted he was a lot younger than she thought:

"Rose: You're 900 years old? The Doctor: Yep. Rose: My mother was right, that is one hell of an age gap."
 * Deb and Lundy on Dexter
 * In Doctor Who, the Doctor and Rose definitely qualify. The difference is about 882 years, as Rose is approximately 18 in the first season of the new series.

"Geoffrey: Oh, you have a son. Not mine, I hope. ... Geoffrey: Ah, Ellen. Where's your boyfriend? Cub Scout meeting?"
 * Also a "hell of an age gap" is Amy Pond and her husband, Rory, since
 * Physically, the Eleventh Doctor and River. Alex Kingston is 48, and Matt Smith is 29. In "The Impossible Astronaut" the Eleventh Doctor jokingly calls River "Mrs. Robinson". However mentally the Doctor is much older than River.
 * An episode of Quantum Leap featured Sam leaping in a man who is 25, and dating a woman who is 50, and has a thirty-year-old son.
 * Al and his girlfriend Tina are also an example. The one time she is shown she appears to be in her twenties or thirties, whereas Al is in his sixties.
 * 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.
 * Ellen and Sloan in Slings and Arrows: neither of their ages are specified, but Ellen's enough older than Sloan that people Geoffrey will often make fun of her for it:

""Well, now I know two things about Iceland. It's where Bjork comes from, and it's somewhere it's possible to fall in something very like love...""
 * Richard at one point mistakes Sloan for a pizza delivery guy, a notion of which Sloan does not immediately disabuse him.
 * Grissom and Sara on CSI. To make things potentially squickier, he was also her supervisor.
 * Shelly and Holling in Northern Exposure. He's about forty years older than her.
 * Quite a common plot device on Star Trek, although most of these are arguably a Mayfly-December Romance.
 * All the Small Things: middle-aged musical director Michael and young soprano Layla.
 * Murphy Brown [older woman] and Peter Hunt
 * Modern Family: Jay is over 60, Gloria is in her 30s.
 * Law and Order featured this with Jack and Claire. Foreshadowed by the fact that the former had a reputation for sleeping with his female assitants, while Claire had been seduced (offscreen) by the much older, married judge whom she had been clerking for as a law student.
 * Law and Order SVU: A thirty-year-old guy and a seventeen year old girl claim to be in love and as bad as that is, she's of legal age. The kicker is that she looks about 12 due to a disease.
 * Depending on how you define age in regards to machines, John Connor/Cameron. John is sixteen, while Cameron is only a couple of years old, and in some ways she acts like a child. A more conventional version of this is implied between the future John Connor and Allison Young; he is roughly forty or so in the future timeline, while she is still in her late teens. Its not made clear whether John and Allison were actually involved, but it is implied.
 * 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.
 * Truth in Television on Rome. Caesar is more than thirty years Cleopatra's senior.
 * And then there's Caesar's daughter married (allegedly happily) to Pompey. 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 British sitcom As Time Goes By began like this, with Jean Pargetter's daughter Judy seducing and then going out on dates with Lionel Hardcastle (who is later found out to be two years older than Jean) and Lionel's young book publisher Alistair Deacon flirting with, attempting to seduce, and finally taking out the much older Jean. By the end of season/series 1, however, Jean and Lionel had reignited their old romance and Judy and Alistair had each given up on their original romantic notions and were beginning a friendship.
 * Dark Angel: Max and Logan had a twelve-year age difference, though you really wouldn't notice without doing the math. Also a real life example, as the actors were engaged.
 * In the made-for-HBO movie The Girl in the Coffee Shop, 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.


 * Darla turned Angel into a vampire and began a long, bloody relationship with him when she was about two hundred years older than him. Even when they meet again during the series, she is still almost twice his age.
 * Not to mention Angel and pretty much anyone else he's paired with.
 * 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.
 * In an episode of Wings, Joe (in his mid-30's) dates Courtney, a 19-year-old. At the end of the episode, she dumps him for another guy. Joe at first takes it in stride, realizing that it would make sense for her to want to be with someone closer to her own age. When he finds out her guy is 45, however, Joe becomes furious. "Isn't that a little old for you?"
 * HBO's Big Love gives us Bill, who is in his mid-forties, and his third wife Margene, who is in her early twenties (and already a mother to two of his children). Apart from them there are 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).
 * The Catherine Tate Show featured the character of Ali, a socially awkward woman who says tactless things to people she meets at parties. In one sketch she embarrasses herself by mistaking a young man's middle-aged girlfriend for his mother.
 * 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.
 * Dallas: In the first season, Lucy has an affair with Ray, who is at least 15 years older than her.
 * In the third season, Lucy dated and got engaged to Alan Beam, who was several years older than her. Later that same season, she dated her teacher.
 * Cliff and Afton, there is at least a 20 year age-gap between them. Later on Cliff and Jamie.
 * In the seventh season, Sue Ellen had an affair with Peter Richards, who was over 20 years younger than her.
 * Beverly Hills, 90210: In the episode "Wild Horses", Dylan enters into a brief affair with a woman at least 20 years his senior.
 * In the fourth season, Andrea briefly gets involved with her college prefessor. Later the same season, Brandon also becomes involved with his teacher.
 * Frasier: In the episode "Fortysomething", 41 year old Frasier is asked out by a 22 year old woman.
 * In seasons 3 and 4, Martin briefly went out with a policewoman named Maureen. She was about the same age as Frasier, who was also interested in her.
 * In season 5, Roz had an affair with a boy at least 15 years her junior, resulting in the birth of her daughter Alice Doyle.
 * In the episode "The Maris Counselor", Martin is asked out by a younger woman. After some nagging by Daphne he agrees to go, only to find out that she actually set Martin up on a blind date with her mother, who was even older than him.
 * Martin dates and eventually marries Ronee, who was once Frasier and Niles's babysitter. Martin is shown initially being uncomfortable with the age difference, but he gets over it.
 * In Fast Track, fortysomething Richard Beckett has a serious relationship with 24-year-old Mimi Chandler. At one point, she accuses him of being more interested in her mother.
 * Almost every Immortal in Highlander. With Methos it borders on ludicrous as literally any relationship he may get into would by definition be a May/December romance, on account of being him the oldest Immortal.
 * The short lived TV series Three Moons Over Milford featured a romance between a woman who was 29, and the main character's son who just turned 16 in the first episode. Though to be fair, he told her he was 20, and when she finds out that he is still in high school, she immediately leaves him and refuses to call him back.
 * The Masterpiece Theater miniseries Reckless, which featured a young doctor beginning an affair with his boss' wife, who is at least 10–15 years older than him. Ironically, the affair is started when she learns of her husband's affair with a younger woman.
 * Downton Abbey has the lovely romance between John Bates (40s, at least) and Anna Smith (20s).
 * Also Edith (20s) and Sir Anthony Strallan (50s), ongoing in a Will They or Won't They? fashion.
 * Yet another example in series two with Mary (20s) and Sir Richard Carlisle (mid-40s to early 50s.)
 * 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 It Got Worse.
 * 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.

Music

 * The old Kurt Weill-Maxwell Anderson standard "September Song" is sung from the viewpoint of the "December" half of one of these. In its original context, in the musical Knickerbocker Holiday, 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.
 * "Hey 19" by Steely Dan.
 * "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 the opinion of this troper that he doesn't end the relationship. Instead, he begs the girl to walk away. This troper's guess is that she doesn't.
 * "40 y 20" (40 and 20) by Jose Jose.
 * "Maggie May" by Rod Stewart. Despite her name, she's the "December" half. And the narrator is well aware that he's nothing more than a fuck to her, but he's too in love to leave her.

Newspaper Comics

 * 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.

Radio

 * 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 his mid-twenties. That's the way it was back then. (There is also a tradition that Joseph was a widower, and that the "brothers and sisters" of Jesus were Joseph's kids by Mrs. #1; making Joseph much older than Mary would also explain why he vanishes from the story, and why if Mary were only the stepmother of Jesus' "brothers" he had to give her to John's care.)

Theatre

 * 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.
 * Also Twelfth Night. Viola must be a fair bit younger than Orsino.
 * In a somewhat more classic comedic example, the elderly Gremio from The Taming of the Shrew attempts to marry the fair young Bianca, although he loses to a younger man.
 * Jokingly invoked in Princess Ida by Gilbert and Sullivan, 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.
 * Gilbert and Sullivan seem to like this one; 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 both The Pirates of Penzance and The Mikado. Both cases are also very one-sided.
 * This is the main plot of South Pacific.
 * Niccolo Machiavelli's Mandragola features the "hot young wife openly cheating on dumb older husband" variant.
 * In The Most Happy Fella, Tony marries Rosabella over his sister's objections that he's too much older than her.

Video Games

 * Griffin (46) and Muffy (30) in Harvest Moon: A Wonderful Life and Harvest Moon DS. They actually get married in the DS games, and in DS Cute, your character (age unspecified but probably in their early 20s at most) can snatch up either Griffin or the 41-year-old Carter for herself as well. There's also a May/September in DS with the PC and Muffy, who's about 10/11 years older.
 * In Tree of Tranquility/Animal Parade, for the ladies, there's also Calvin and Jin. Neither of them has a directly specified age, but Calvin alludes to a fairly large age difference between him and the PC (it's possible he's younger than her, since he's explicitly called a "Young Man," but he's pretty rugged-looking for that), and Jin is old enough to Jin can also marry Anissa, who's probably about 20.
 * In Magical Melody, although no specific details regarding age are given in-game, Eve's response to your marriage proposal to her clearly implies this trope is once again in full force.
 * And all of this is to say nothing of the series' fondness for Mayfly-December Romance...
 * In Fire Emblem (AKA Blazing Sword in Japan), 16-year-old White Magician Girl Serra has three possible love interests. One of them is Genius Bruiser Oswin, who is not only much taller than she is, but is also in his early-to-mid thirties (and he looks even older, much to his own dismay)
 * Also, supplementary materials hint that another love interest of hers, the Fragile Speedster Matthew, is in his mid-to-late 20's. Really, Serra seems to have a thing for older guys; the only suitor of hers who's around her age is Erk.
 * 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.)
 * In the sequel Sword of Seals, three of Roy's five love interests are girls in their teens. There are two exceptions, however: one of them is his Sexy Mentor Cecilia, a woman in her early-to-mid 20's who trained both him and Lilina.
 * There's also Sothe and Micaiah in Fire Emblem Tellius. She's Branded and way older than him despite looking young; she met him when he was just a boy. At the end of the game, if you get A support for them, they get married.
 * Not to mention the two Dragon Riders Haar and Jill. There's a visible age gap between them, an not to mention he worked with her father Shiharam, but they'll still get married if they have an A support.
 * In Seisen no Keifu, you get a sofer case of this whenever you pair up Shanan or Oifaye with anyone in the second half of the game, since they're adults in their late 20's or early 30's while the girls in the Liberation Army are more often than not in their mid to late teens.
 * Also, in Fire Emblem Thracia 776 there's Olwen and Fred. They get married after the war, and Fred's ending says he got often teased for being older than his wife as well as her former bodyguard.
 * '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:
 * The Juno (male) ending (not canon) in Soul Nomad and The World Eaters plays with this. Revya is 18, shes 28.
 * Get this ending while playing as a Female, and 11-year old Penn will ask Revya to marry him.
 * In the other endings, the Nereid Wife Husbandry plan may come to fruition six years later, with Juno being 34 at that time.
 * A lesbian example can be found in Heileen, as one of the endings pairs up the protagonist Heileen (age 18) with Lora (age 36). Mind you, Lora doesn't look that much older than Heileen.
 * This trope is particularly common in otome games. Most often, you can pair the heroine (who is usually in her teens or early 20s) with a bishonen who is twice her age.
 * One of the love interest for your daughter in Princess Maker 5 is at least 39 while the former is 18 at the end of the game. And of course there is the Wife Husbandry option for the whole series.
 * Tales of Symphonia manages to combine this with Mayfly-December Romance in one of the endings. Raine is a member of a species whose lifespan is around a millennium or so, and Lloyd is her teenage student. At the same time, she's only 23.
 * Played straight with Regal and Alicia, as he's well into his twenties when she's a teenager. Also, in the ending where Lloyd ends up with Presea, difference largely goes unnoticed since she looks to be five years his junior, when she's actually a decade his senior.
 * Gets even squickier if you consider that  and, while it's not said exactly how much younger Alicia was, it could be that Regal was in his early twenties and Alicia might've been a pre-teen.
 * The animated adaptation clears everything up. Presea was chosen sixteen years prior to the story's beginning after their father died rather than . This means that Regal, who is thirty-three in the present time, was nineteen when . Now, consider that Regal's butler mistakes Presea for being the "younger sister" in-game. This implies that Alicia was a few years older than her when . Therefore, Regal and Alicia must have gotten together in their late and early-mid teens respectively, which is considerably less Squicky than a twenty-something running around with a pre-teen. The only Mind Screw remaining is how Regal was the president of the the world's biggest "Do Everything Company" at nineteen.
 * He inherited the position?
 * There's also
 * This trope is actually debated in one of the skits - before Lloyd and co. find out why Regal seemed so interested in Presea (it was because she ), Lloyd, Genis and Zelos debate why he seems so interested, with this trope being the main reason they come up with. Genis and Lloyd both brush off the idea, since he's much too old for her...only for Zelos to say that the idea's not actually that far-fetched, and that he once knew a noblewoman who married a man thirty years her junior. Lloyd seems quite horrified, while Genis is just angry since he likes Presea himself (obviously, Regal doesn't like her in that way - doesn't stop this from being a hilarious skit).
 * This is often not noted, but Star FOX has Fox himself with Krystal; by Assault, he's 27 and she's 20.
 * Tales of the Abyss has a complicated version of this trope.
 * Comes up in Clannad where in Sagara Misae's route, the 17 year old Tomoya falls for mid-twenties Misae. Also, Kouko Ibuki and Yoshino Yuusuke, though they both look very young.
 * Colonel Volgin and Major Raikov in Metal Gear Solid 3. 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).
 * What about Snake and Meryl? He's an old-looking thirty-two year old, she's eighteen.
 * 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.
 * Drakengard 2 has this with The Hero Nowe and, with the former being around 18 while the latter is 26.
 * The first incarnation of Fei and Elly in Xenogears. She's probably in her early 20s (at least physically) and he's probably no older than 13 when they first meet.
 * There's also Cyan and his wife Elayne; you never learn exactly how old she was, considering that she's killed in Doma near the beginning of the game, but we know that Cyan is in his late fifties, that Elayne appears to be a young woman (IOW, the game uses the sprite for young villagers to represent her) and that the two have a young son. Also, Cyan carries on a sort of long-distance romance with another young woman named Lola much later in the game, complete with hand-made silk flowers and long love letters.
 * Granted, those letters and flowers he sent her were more of a comfort to spare her the news that her boyfriend died about a year ago.
 * Terra is shown to have had an attraction (although possibly a platonic one - it's not clear) to General Leo, who was thirty. (Fan pairings of Leo and Celes also fall under this trope.)
 * Setzer also flirts with Celes, and attempts to convince her to marry him in exchange for his help (she finds a way around it.) The whole reason that Setzer is talking to Celes is because she was impersonating Maria, an opera singer that Setzer fancied; she took Maria's place the night he planned to sweep her away. Setzer is also twenty-seven. We never learn how old Maria is, but presumably she's close to the same age as Celes.
 * Some of the love interests in Avalon Code have significant age distance with the main characters (who are roughly 13-15), most notably and, who are in their twenties. And then there are the Book Spirits...
 * In Persona 3 Portable, it's possible for the Female Protagonist (about 16) to initiate this with the 10 year old Ken Amada. However this requires her to have Max Courage (quite literally, be a Badass) in order to get over the social stigma of such a relationship.
 * Not in the western release.
 * All up to interpretation. You did promise the kid you'd wait for him.


 * Butch and Charlotte in Guilty Party. Their exact age difference is unknown, but Butch is probably in his 40's (at oldest) and Charlotte is at least 60. They've been married for long enough to have an (adopted) daughter in her mid teens... and they are still very much in love.
 * There's also a much better instance of this trope implied at some points in the manga and the Hachiyou Shou TV anime adaptation: Tomomasa and Fuji-hime. The former, as noted above, is 32; the latter is ten. This is hardly portrayed as disturbing, just embarassing (but then, so are the scenes of Tomomasa flirting with Akane). Might have to do with Haruka being set kinda-sorta during the Heian Period, though, so maybe the entire thing is justifyed to an extent.
 * Commander Shepard and Liara T'Soni from Mass Effect. Shepard is 29, Liara is 106. Justified in that she's a Space Elf that ages differently—by human standards, Liara is only in her mid twenties.
 * In Mass Effect 2, Shepard (now 31) has the opportunity to engage in a bit of light romance with two asari—Samara, nearly a thousand years old, and, in her 400s. Neither ends well; while Samara is attracted to Shepard if s/he is mostly Paragon, she is too committed to her Code to start a relationship. Shepard can sleep with
 * The May/September version also applies to some of the other pairings. For Male!Shepard, there is seven years between him and Jack/Tali; Gender Flipped with Miranda, who is four years older than Shepard. For Fem!Shep, there is seven years between her and Thane (he's 38, she's 31); the only one spared is Garrus, who's supposedly the same age than Shepard and have the same life expectancy. Add/subtract two years if you want to include the time Shepard was unconscious.
 * Gordon and Alyx in Half-Life 2... maybe. While they were born nearly 20 years apart, Gordon's time spent in stasis erased that age gap.
 * Ezio Auditore (52) and Sofia Sartor (35) at the end of Assassin's Creed: Revelations. The Embers animated short reveals that they marry and end up having 2 children. Then.

Web Comics

 * Narrowly averted in Megatokyo by virtue of the fact that Piro has shown no interest in pursuing a romantic relationship with any of young women (Yuki, Ping) who seem to be attracted to him (and in all fairness, he's not that much older than they are).
 * Ping might not count as she is non-organic and able to change her appearance, and presumably her apparent age.
 * Although Junko—until recently a relatively minor background character—has admittedly made a practice of dating older men, there has been no indication in the comic that these relationships are anything other than financial.
 * Mr. Mighty and his wife Jane in Everyday Heroes have the May/September type of romance; he's about 10 years older than her.
 * Played with in True Villains, where ten year old Mia has a crush on Bayn. He's over eighty years old,
 * In Sinfest, Monique dismisses an old man as seeking this to relive his youth.

Western Animation

 * 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.
 * Apu and Manjula were shown to be relatively the same in age in "The Two Mrs. Nahasapeemapetilons", though. The Simpsons is notorious with its regard to continuity.
 * A recent episode had 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 also Comic Book Guy and the elderly Agnes Skinner.
 * Selma also fell in love with Homer's father.
 * 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.
 * Ferb's Precocious Crush on Vanessa Doofenshmirtz in Phineas and Ferb. Word of God says he likes to imagine them getting together "when the age difference won't matter so much."
 * Mac's crush on Frankie in Foster's Home for Imaginary Friends, though that's more of a Precocious Crush, really—there's no sign of reciprocation.
 * 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 young-looking guy - a phenomenon often observed in Mayfly December Romances. Also, he's made of pages from the book he's trapped in, which serves to distract. Whether or not that relationship would qualify as a Mayfly-December Romance is uncertain, due to the natures of the characters.
 * In The Legend of Korra, Korra's Airbending teacher Tenzin is 51. He's Happily Married to Hot Mom Pema, who is 35 and pregnant with their fourth child. Their oldest child is 10, so when they met she was at most 25 to his 40.

Real Life
"Barbi Benton: "I don't know, I've never dated anyone over 24 before." Hugh Hefner: "That's all right, neither have I.""
 * In Victorian times, the May–December Romance was considered not just normal, but desirable. Since all but the poorest women were not supposed to work outside the home after marriage (and were often not allowed to, through legal and other means), a man had to ensure he earned enough to support a family before he married, and that often meant delaying marriage for ten or more years until his income was high enough. On the other hand, women were expected to marry fairly early (earlier than in previous centuries) so they could have the large families that society expected. It was therefore considered somewhat shocking for a woman to marry a man her own age; women were encouraged to marry men ten or more years older than they were, and long engagements of over a year were considered - not shocking, really, but utterly stupid. Those who find May December Romances in Victorian literature shocking are in fact experiencing Values Dissonance.
 * Furthermore, there was a 'cult of the child' among the Victorian middle and upper classes: child actresses were adored and it was quite in vogue for undergraduates to treat little girls to tea and boating on the river. Undoubtedly there was an erotic undercurrent to some of these friendships, though, paradoxically, it was the 'innocence' of the little girls that people idealised. Meanwhile, poor children laboured in mines and factories and up chimneys, or else as prostitutes.
 * Actually, it goes back far further than the Victorians. It was the norm throughout most of history. It let men get established well enough to support a family before starting one, but there was also the high female mortality rate in childbirth—the older a man was, the fewer women his own age there were, married or not.
 * Not entirely accurate: despite general perceptions, the norm in Western Europe since around the sixteenth century has been late marriages for both sexes with relatively narrow gaps between spouses, only a few years on average. May December Romances were hardly unknown, but they were a minority.
 * Older Than Feudalism: Back in ancient Athens, the average man got married at 30, to a woman of 14. Spartans, on the other hand, were considered pretty weird in that their 20-year-old boys married 18-year-old girls.
 * Khadija, the first wife of the prophet Muhammad, was 15 years older than him. Oh, and she was also his boss. They were Happily Married until her death.
 * Aisha, one of his other wives, 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 sidekick/Number Two/eventual successor Abu Bakr al-Siddiq.
 * Peter Abelard and his pupil Heloise fell madly in love after he began to privately tutor her - in more than one way. He was 22 years older than her. When her enraged relatives permanently separated them, they continued to write passionate letters to one another until they died.
 * Henry VIII with Anne of Cleves (24 years younger) and Katherine Parr (21 years younger). The wife between those two, Katherine Howard, was younger than Henry's eldest daughter.
 * German satirist, physicist, and small-time philosopher Georg Christoph Lichtenberg, 38, and looking far older from a spine-related hunchback condition, and Maria Stechard, 13! In an odd twist she died first, only five years later. Unfortunately it turns out he wasn't just an old lech as others in Darmstadt suspected, as he never got over it.
 * Antoine Lavoisier, father of modern chemistry, married a 13-year-old girl when he was 28. This was not uncommon at the time (the 1770s). Though he kept a long-term mistress, one nearer his age, he seems to have had a loving relationship both with the mistress and with his wife, who knew about the mistress. His wife was a substantial help to him: she translated scientific documents from English into French so that he could read them, did drawings and engravings of his and his colleagues' lab instruments, hosted parties at which scientists discussed chemistry, and translated and edited her husband's memoirs. Tragically, Lavoisier was executed in The French Revolution.
 * Tenth U.S. President John Tyler was 54 when he married his second wife, 21-year-old Julia Gardiner. She was younger than three of his eight children by his first wife, and they had seven more together. His youngest son with Julia lived into the 1930s; about ten years before his death he married a younger woman too, and had a number of children. As of 2009, two of his sons are still alive. Your grandfather may have been born during Roosevelt's or Truman's presidencies, or perhaps even Harding's or Coolidge's or Hoover's, and his grandfather might have been born during Polk or Tyler's or Jackson's: those men's grandfather was born during Washington's presidency.
 * Also Grover Cleveland, whose wife Frances Folsom was twenty-nine years younger than he.
 * He was also her late father's business partner, and she grew up calling him "Uncle."
 * When a reporter asked him why he wasn't married yet, he replied: "I'm just waiting for my wife to grow up."
 * In 1829, 33-year-old Michael Morris Healy, an Irish immigrant to the US who had become a successful planter, took his 16-year-old slave Mary Eliza as his common-law wife. They lived together until their deaths a few months apart in 1850. She bore him ten children, of whom nine survived to adulthood. Healy provided for their education and they were remarkable for their achievements.
 * Most of Edgar Allan Poe's relationships were with women his age or older, but at age 27 he married his 13-year-old cousin, Virginia Clemm, though he apparently refrained from consummating the marriage until she was 16. They seem to have been a happy, mutually devoted couple. Her death from tuberculosis at age 24 sent Poe into a deep depression.
 * Charles Dickens was a married father of forty-five when he met actress Ellen 'Nelly' Ternan. She was eighteen. He fell in love with her and ended up leaving his wife for her.
 * John Ruskin was a towering figure of Victorian Britain: art critic, social thinker, philanthropist, draughtsman, watercolourist, writer on a very wide range of subjects. He married Effie Gray, nine years younger; she was the child of family friends, and he had written a fantasy novel, The King of the Golden River, for her when she was 12. However, Ruskin never consummated the marriage, and she was eventually able on these grounds to get an annulment and marry Pre-Raphaelite painter John Everett Millais, who was the same age as her. Ruskin was a benefactor to a progressive girls' Boarding School; he played with the girls when he visited and corresponded with various individual girls. As he grew older he spent a lot of time with the children at another school. In a letter—to his father! -- he described the beauty of a girl of 10 or 12, seen half-naked on the beach, whose breasts were only beginning to develop. Elsewhere he wrote in childish language about a crush on a 15-year-old girl. He admired the work of Kate Greenaway, a celebrated illustrator, best known for her drawings of children, and asked her to draw the children naked. His great love was undoubtedly Rose la Touche, 30 years younger than he, to whom he taught drawing. He met her when she was 9 and seems to have fallen in love with her when she was about 11; he was friends with her mother as well. Ruskin and Rose kept up a long, affectionate correspondence. When she was 18, he proposed to her; she said no but told him he could ask again in three years, when she'd be of age. He did, and she refused again. This was because of their religious differences and also because Rose's parents were dead set against the match: Ruskin's first marriage had been annulled on the ground that he was incurably impotent, but he probably wasn't, and if he should have children with Rose, the annulment would become invalid and Rose's children would be illegitimate. Rose suffered from some sort of mental illness. She died in an asylum aged 27, and Ruskin was heartbroken.
 * Fyodor Dostoevsky married his second wife, Anna Snitkina, when he was 45 and she was 20. Despite some early bumps (caused mainly by Dostoevksy's gambling addiction), the two ended up quite happy together.
 * Some of Dostoevsky's writings indicate that he was probably drawn to girls in their early teens and even younger, but felt guilty about it.
 * Lewis Carroll, mathematician, logician, pioneering photographer, Anglican deacon and children's author, had a series of "child-friends", almost exclusively female ("I like all children -- except boys.") The most famous was Alice Liddell, namesake of Alice in Wonderland, but there were many more, including his other great love, Gertrude Chataway, for whom he wrote The Hunting of the Snark. He met her at the seaside when she was 9 and, though his friendships with other little girls often ended when the girls got to be about 14, the age of pubescence in those days, Gertrude was still taking seaside holidays with him when she was in her late 20s, shortly before his death.
 * Although bi-sexual Hans Christian Andersen had a couple of unrequited loves in his life, some speculate that he managed to enter an intimate relationship when he was in his late 50s, with a dancer named Harald Scharff, who was in his early 20s.
 * Frederic Shields, an artist, art critic, illustrator and designer of Victorian Britain, associated with the Pre-Raphaelite Brotherhood, was brought up in extreme poverty. As an adult he met Matilda Booth, a little girl also from a poor family, and she modelled for some of his paintings. He gave her private lessons in reading, manners etc. for several years, then married her when he was 41 and she was 16 or 17. They adopted Matilda's toddler sister Jessie soon after their marriage, and sent her to school for several years. However, the marriage was not a success and Shields soon shipped Matilda off to a select Boarding School for 'young ladies.
 * William Holman Hunt, one of the founders of the Pre-Raphaelite Brotherhood, the most famous religious painter of his day, initially had an affair with a young barmaid, Annie Miller. Like Shields, he had her educated, but she had an affair with a lord and was seen around with other men, then upped and married someone else. After this Hunt turned to Fanny Waugh, who died of puerperal fever six weeks after bearing him a son, and not long short of their first wedding anniversary. Fanny's sister Edith, thirteen years younger than Fanny, had fallen in love with Hunt at first sight when Edith was fifteen and Hunt thirty-five. As Hunt painted a portrait of Edith for her twenty-first birthday, he fell in love with her in return, but they both felt guilty about dishonouring Fanny's memory. Some years later they finally got married, but had to go to Switzerland to do it, as at the time it was incest in England to marry your dead wife's sister.
 * Pre-Raphaelite sculptor Thomas Woolner married Fanny and Edith's sister Alice, who was twenty-one years younger than him. Woolner too had initially been in love with Fanny, but she had refused him. Woolner considered Hunt's marriage to Edith immoral and never spoke to Hunt again after it.
 * Victorian Edward Burne-Jones, pre-Raphaelite painter and the best British designer of stained glass in his century, was married to Georgiana 'Georgie' MacDonald, the sister of a school friend of his. She fell for him when she was 12 and he was 19. They were largely separated while he was at Oxford, but began courting seriously when he was 22 or 23 and she was 15. He proposed shortly before her 16th birthday and, having obtained her parents' permission, they got engaged when she was 16 and married four years later. After they had been married for some years, Burne-Jones fell in love with Maria Cassavetti Zambaco, a slightly younger woman who had previously had a disastrous marriage to a much older man, a doctor. In later life, Burne-Jones had a series of chaste, decorous friendships with young women, and felt sad when they grew up and got married. One of his favourites married a man 15 years older than her. Then, 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. Throughout all this, Georgie remained devoted to her husband.
 * Georgie was friends with Mary Ann Evans, aka George Eliot. After the death of her longtime partner George Henry Lewes, a man her age, Eliot married, at the age of 60, John Cross, a 40-year-old longtime friend whom she had always affectionately called "nephew". This May/December marriage, like her openly adulterous relationship with Lewes, shocked everybody. Eliot fell ill and died seven months after the wedding.
 * Possibly, Mark Twain. As an old man he had a small circle of little girl friends, aged about 10 to 16. They wrote him affectionate letters. Whether his feelings for them were simply grandfatherly fondness or had a tinge of the romantic and/or sexual is unknown.
 * Francis Kilvert, a kindly young Victorian clergyman in a village on the Welsh border, kept a series of celebrated diaries. These make it apparent that he was attracted to and crushed on a series of little girls: for instance, he has a thing for 'Gypsy Lizzie', who is in his reading class, he likes the looks of a pair of girls about 12 and 14 years old, and when visiting a parishioner he is overwhelmed with emotion when her 7-year-old daughter sits on his lap and hugs and kisses him. His diaries also record an interest in girls' bottoms and in the whipping thereof. At 30, he fell in love with a 19-year-old girl fresh from school, but her father would not permit a marriage, not because of the age difference but because of Kilvert's lack of money.
 * Lord Baden-Powell, founder of the Scout Movement, married 23 year old Olave St. Claire when he was 55. Though they had a son together, Baden-Powell's true sexual interest seems to have been in adolescent boys. He also was friends with and corresponded with a series of little girls.
 * Victorian Francis Thompson, failed priest, failed doctor, opium addict and poet, liked little girls and fell in love with two of the 10-year-old daughters of a couple he was friends with. Seems that when one got too old for his liking, he transferred his affections to her younger sister. His tombstone says, "Look for me in the nurseries of heaven."
 * Louis Wain, the man who drew the anthropomorphised cats, at the age of twenty-three married his sisters' governess, Emily Richardson. She was 10 years older than him. This was quite scandalous back then. She died of cancer three years after the marriage.
 * 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.
 * Chaplin had a habit of falling for teen girls. His youngest crush was only 13. He did not have sex with her, but he did have sex with several girls who were just a few years older than that.
 * Raissa Myshetskaya went to the Paris Conservatory to study music and married her teacher. They had two daughters, Nadia and Lili Boulanger. Their father was seventy-one when Nadia was born and seventy-six when Lili was born. Both girls were musical prodigies. At age nineteen, Lili became the first woman to win the Prix Rome. She died of Crohn's disease at twenty-four. Nadia, who had entered for the Prix Rome four times without success, decided that her gifts as a composer were inferior to her sister's and dedicated her life to music teaching instead, becoming, in the view of composer Ned Rorem, "the most influential teacher since Socrates"!
 * Peter Llewellyn Davies MC, one of the five adopted sons of J. M. Barrie (Peter Pan), was 20 when he had an affair with 47-year-old Hungarian-born professional artist Vera Willoughby, whose daughter was older than Peter. Barrie and Peter's former nurse, Mary Hodgson, were both scandalised. However, this was 1917, and Peter had lost both of his parents as a child, then lost his brother George, to whom he had been close, in the war, and then suffered from shell-shock—so his violation of social norms is certainly understandable. The relationship continued for at least two years.
 * Conservative politician Baron Boothby was bisexual and had numerous affairs on both sides of the fence. He was married twice, and his second wife was thirty-three years younger than him.
 * 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, but Miller's daughter had always been against the relationship and within a few hours of Miller's death she ordered Barley to take her things and leave the house.
 * 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.
 * Michael Douglas and Catherine Zeta-Jones. Douglas is exactly 25 years her senior.
 * And he's older than her father, even!
 * Harrison Ford and Callista Flockhart. Ford is 22 years her senior.
 * Hugh Hefner. Specifically his now ex-fiance (who bailed five days before the wedding), Crystal Harris, is a full sixty years younger.
 * "Hef" had a habit of becoming involved with much-younger women. The Other Wiki reports that, in 1968, then-42-year-old Hugh Hefner asked then-18-year-old Barbi Benton to go out on what would become their first date in a relationship that lasted seven years.


 * And Agatha Christie, whose long and happy second marriage was to a man fourteen years her junior. Although he did cheat on her.
 * Christie's first marriage was a May–December Romance in the other direction; her first husband was almost fifteen years older than her. He cheated on her too, but so outrageously and so openly that she either went nuts or tried to frame him for her murder.
 * Author Christopher Isherwood and painter Don Bachardy.
 * Hugh Jackman and Deborra-Lee Furness, whom he met at the age of 27 while starring opposite her in the romance/drama show Correlli. Accounts place her as between eight and thirteen years his senior. It doesn't seem to matter much, as theirs is one of Hollywood's few truly happy marriages. There is much Yoko Oh No on the IMDb boards, however... probably from sheer jealousy.
 * Clint Eastwood is a good 35 years older than his wife.
 * As is Woody Allen.
 * Lauren Bacall and Humphrey Bogart. They began dating when she was nineteen and he was forty-five, married the very next year. His nickname for her was 'Baby'.
 * Actor Jeff Goldblum (born 1952) is dating actress Tania Raymonde (Malcolm in the Middle, Lost) (born 1988).
 * 72-year-old Italian Prime Minister Silvio Berlusconi, probably the most unorthodox state leader on the planet, has been paired with numerous women, most notably 18-year-old model Noemi Letizia. Naturally, this has caused something of a stir.
 * It reached Memetic Mutation levels once photos from the party where Noemi looks like badly pasted in with Photoshop reached public domain. Here's a video made from the thousands of pictures made for a particular blog, all starring very special guests. (Warning: many Italian personalities abound).
 * In a new episode of this never-ending, most shameful show, we are introduced to Karima El-Mahroug, aka Ruby Rubacuori (lit. "Ruby Heartthief"), a young Moroccan girl who's apparently been living as an escort for the last few years. When she still was underage, she might have been repeatedly attending Berlusconi's sex parties at his place. He even admitted having given her money (around 7,000 Euros), of course not in exchange of any sexual favour, but merely because she was "in need" and he's such a generous guy. So generous in fact, he intervened when she was arrested in Milan for petty crimes and managed to have her released against regular procedures, by telling the police she had been reported to him as then-Egyptian president Mubarak's niece. It is still not clear whether she'd had sex with him or merely attended to his sex parties to dance scantily-clad.
 * To clarify, the age of consent in Italy is 16, and non-brothel prostitution is legal. However, it's illegal to pay for sexual services with a minor (anyone under 18). So it wouldn't be illegal if Berlusconi had simply had sex with Ruby (who was 17 at the time), but it would be illegal if he paid her to have sex with him.
 * The late Anna Nicole Smith (age 26 at the time) married oil magnate J. Howard Marshall when he was 89. She claimed it was "real love", but everyone else knew what was going on, of course - especially after she got involved in a protracted courtroom drama with his family over the inheritance after he died.
 * 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.
 * For about two years, Heath Ledger dated Naomi Watts after they met on the set of Ned Kelly. She was 11 years his senior.
 * 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.
 * Dame Margot Fonteyn, prima ballerina assoluta of the Royal Ballet and one of the greatest classical ballerinas in history, and her best and most famous partner, Rudolf Nureyev. While there is no absolute proof they ever consummated their relationship, it is quite probable that they did, and they remained each other's dearest friend and confidante until Fonteyn's death in 1991. The shocker? Fonteyn was nineteen years his senior, and in fact was at the point in her career when most thought she would retire when Nureyev arrived in England. Instead, they would dance together for another fifteen years.
 * Except... Nureyev was quite openly gay. They were more The Straight Will and Grace.
 * So it was a May-December Friendship?
 * Or If It's You It's Okay?
 * Cleopatra and Julius Caesar are probably the Ur Example of this trope. They met when she was 21 and he was 52.
 * Canadian Prime Minister Pierre Elliott Trudeau (himself highly unorthodox but also very effective) met his wife Margaret during his stint as Minister of Justice while vacationing in Tahiti in 1967. She was 18. He was 47. He became Prime Minister next year; they got married in 1971; had three kids; and the marriage got shot to hell. Did we mention that she was something of a hippie and partied with (and supposedly had an affair with) Mick Jagger?
 * Adolf Hitler was almost 23 years older than Eva Braun.
 * 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.)
 * Tom Cruise, born in 1962, and Katie Holmes, born in 1978. You just know she was fantasizing about this when she was 13 and watching Far And Away.
 * German actor, entertainer Johannes Heesters (born 5 December 1903) has been happily married for 20 years to wife Simone Rethel born 1949.
 * Kevin Kline started dating Phoebe Cates in 1983 and they've been married since 1989. She is 16 years his junior.
 * Russ Banham (57) and Jennifer Sue Johnson (mid-30's)
 * The National Geographic Channel series Taboo dealt with a couple that met when the man was 18, and the woman was 50. The age gap is so dramatic that his wife is actually older than his parents.
 * The 2011 marriage of actor Doug Hutchison (51) and aspiring singer Alexis Stodden (16) with parental approval.
 * Aristotle Onassis has married many women who were born in 1929. He was born in 1906.
 * There's allegedly a biological basis for it. Women genetically tend to be attracted to higher-status men with more resources, while men as a rule have it hard-wired to prefer young, presumably fertile women. It comes down to that reproduction thing. Mandatory Disclaimer - Before someone flies off the handle, these are tendencies and not absolutes, and they have not moral but evolutionary rationales. Simply put, way back when it was better to be the wife (or even concubine) of a high-status male than of a better-looking dirt-farmer.
 * 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. That now-modest pension spanned three centuries.
 * Guitar legend Ritchie Blackmore (born in 1945) and his wife, creative partner and co-founder of an eponymous Folk Rock band Candice Night (b. 1971). They've first met in 1989, when Ritchie was 44, and Candice 18, and basically have been together ever since. Notably, Candice is seven years younger than Jurgen Blackmore, Ritchie's son from his first marriage (who's also a musician).