May–December Romance Cleanup

Incorrect, misuse (18/50) 36 %

• 1 Characters.A Song Of Ice And Fire Other Westerosi: Ramsey's mother. Her first husband was twice her age. Not that it mattered, since he was dead soon after.
• 2 Characters.Americas Next Top Model Cycle Eight: She was 18 when she married her 40-year-old husband. It is implied that she's a Mail-Order Bride.
• 3 Ora Cle: Depending on the Author: In the 60s, she was at least seven years older than Dick Grayson. However, it wasn't until the 90s (after Batman: The Animated Series) when DC Comics began to seriously push the Grayson-Gordon relationship, where her age is implied to be much closer to that of Dick's, due to them being Childhood Friends. In Batgirl: Year One, she seems to be 2-3 years older, at most. (She has now been retconned to the same age as him thanks to Flashpoint. They were already about the same age in earlier works such as Batman: TAS.)
• 4 Fanfic.Between My Brother And Me: Played for drama. Raphael is at least in his 20's, and May is 10 years old. Raphael is obsessed with her only because she looks like his supposed savior. May, naturally, doesn't understand what is going on and is freaked out at the whole idea. Still, it doesn't stop Raphael from continuing to pursue a lover at least half his age.
• 5 Fanfic.All You Need Is Love: Naomi is ten years older than Light.
• 6 Fanfic.Mr And Mrs Gold: As Belle and Rumpelstiltskin, she is in her early twenties while he is literally hundreds of years old. As Rose and Mr. Gold, Emma was sure that he was her father or father-in-law before she saw them kiss. Emma even once refers to Mr. Gold as a “cradle-robber.”
• 7 Film.Blood Work: When this movie was made Eastwood was 72 and Wanda De Jesus, who played Graciela, was 45. Reviewers singled out the romance plot thread as one of the weaker points in the film (in the novel, Mc Caleb is 46).
• 8 Film.M Anhattan: Ike (42) and Tracy (17).
• 9 Friends.Tropes K To O: The show had the episode "The One With The Rumor", where it was revealed that Ross made out with his librarian in high school, she was 33 years older than him. Not really a Romance Relationship, though.
• 10 KimPossible.Tropes M To R: Drakken and Shego. He's the same as Kim's father (his early 40s), while Shego is somewhere in her twenties by the series' end.
• 11 Theatre.The Lady From The Sea: Bolette, in her early twenties, falls for her former teacher, at least ten years older than she is. And then there is Ellida, implied to be much younger than her husband the doctor.
• 12 VideoGame.Cute Knight Kingdom: One of the romance options is John the innkeeper, who appears to be at least ten years older than the PC (who is 20 at the time he can propose).
• 13 VideoGame.F Zero: The Arrows, possibly. He's eight years her senior (as of GX, he's 35 and she's 27), but it's unknown when they first met. (So, May-September Romance?)
• 14 Characters.Ex Heroes: Slightly downplayed: there was an eleven-year gap between him and Banzai.
• 15 Characters.Imperium Nova: Rosetta is 18 years younger than her husband. By the time Ehno became Emperor, she was 35 while he was 53.
• 16 Characters.King Of The Hill The Hills Family And Other Relatives: Between Cotton and Didi, he's in his seventies and she's roughly forty. Didi and Cotton's son Hank even went to kindergarten together.
• 17 Characters.The Tudors: Charles V, Holy Roman Emperor. Betrothed to Mary when he is 25 and she is six. He later jilts her for Isabella of Portugal.
• 18 Film.After The Sunset: Was Sophie and Zacharias (she's 25 years his junior).

Murky/vague or zero-context (24/50) 48 %

• 19 No Ein: One-sided, anyway—Kuina is in love with Kosagi but appears to be much older than her.
• 20 Anime.Overman King Gainer: Mamahd and Liubov.
• 21 Anime.Star Driver: Mr. Watanabe is 65. Mrs. Watanabe is 15.
• 22 Characters.And Then There Were None: Implied among him and Leslie, which explains why she ultimately turned to a much younger man.
• 23 ComicBook.Dallas Barr: Sarabande and Dallas posing as Lord Stileman. Implied to be common among immortals in general, the younger looking trophy wife not always being May...
• 24 Fanfic.The Boy Who Died A Lot: commented out ZCE
• 25 ComicStrip.Judge Parker The aforementioned Cedric even describes himself as having a weakness for younger women.
• 26 Fanfic.We Were Friends: ZCE
• 27 Literature.Mrs Dalloway: Peter Walsh is in the process of divorcing his wife for a much younger woman.
• 28 Literature.Sputnik Sweetheart: Of a sort, between Sumire and Miu.
• 29 Literature.The Scarlet Letter: Hester and Chillingworth had a marriage of this at the very least.
• 30 Literature.The Quiet American: Fowler is past middle age while Phuong is barely out of her teens.
• 31 Theatre.My Fair Lady: What may have happened between the 21-year-old Eliza and the much older Higgins, who is at least twice her age.
• 32 VisualNovel.The Second Reproduction: Perfectly Arranged Marriage: For Christina's older sister, despite it being a May–December Romance.
• 33 Webcomic.Joe Loves Crappy Movies: Parodied when Tom Cruise brings out Dakota Fanning instead of Katie Holmes.
• 34 Webcomic.The Kingdom Of Naroni: Aldhein and Alsina, and later Falidor and Raia.
• 35 Characters.Heroes Rise: Jenny Yu/Null. Not as extreme as some, but one reason she's hesitant to start a romance with the PC is because she's several years older than them.
• 36 Characters.Jane The Virgin: Catalina. She's married to a much older French nobleman.
• 37 Characters.Holly Oaks: Teresa. With Patrick Blake.
• 38 Literature.Whos Afraid Of Beowulf: Hinted at between Arvarodd and Hildy, only there wasn't time for much actual romancing.
• 39 Literature.Wicked Lovely: Due to the immortality of the fey, pretty much every couple except Aislinn/Seth and Niall/Irial.
• 40 FanFic.The Obsidian Dawn: Think the 10,000 year gap between Onyxia and Fordragon is creepy? Nalice and Serinar have almost thirty thousand years between them.
• 41 Characters.Went Worth: Vinnie. With his young "tart".
• 42 Characters.Twin Peaks Residents: Andrew was much older than Josie when they married.

Correct use or fairly OK (8/50) 16 %

• 43 Characters.A Brief History Of Equestria: Commander Hurricane. His wife Clover was young enough to be his granddaughter.
• 44 ComicBook.Sin City: Nancy and Hartigan. He doesn't go so far as to actually sleep with her, since he understandably thinks he's way too old (around 65 at the end of the story) to enter a relationship with a 19-year old, but they do share several very passionate kisses and he describes her as "the love of my life" in his internal monologue. Hartigan explicitly rejects the relationship due to the age difference.
• 45 Film.First Knight: Arthur is 35 years older than Guinevere, though such age differences were probably quite common in those days.
• 46 Film.The Lonely Lady: The barely out of high school Jerilee and the 50-something Walter.
• 47 Literature.Three Act Tragedy: Sir Charles Cartwright, 55, is in love with Egg, 25, though he fears that she prefers her old friend Oliver Manders, who is much closer to her age. Egg, on her part, hero worships Sir Charles and happily accepts his attentions.
• 48 WebVideo.The Angry Grandpa: Lauren seemed to be several decades younger than Grandpa when the two of them dated and later got engaged before his passing.
• 49 Characters.Ultimate X Men: May December Cheating. Jean (20-something) is the May to Logan (about 80-ish) in the first arc.
• 50 Film.Harold And Maude: The big one, and an extremely rare gender-flipped variant. Young man Harold pairs up with the aging Maude. He's 20. She's 79. It's a big love.