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Anime and Manga
- Haré+Guu Deluxe has an example going in line with May–December Romance. The Muscular bank robber ends up with the elderly Dama in a case of Love at First Punch.
- Shiro's parents in Jubei-chan.
- Invoked in Spice and Wolf: Lawrence explains that Horo (who he introduces as "my wife") is hiding her face in a cloak because she's embarrassed by her horrific burn scars. In fact, Horo is hiding her Unusual Ears.
- Sumiyoshi's parents from the Excel Saga manga. His father is a "normal" attractive anime guy, while his mother looks like a girl Sumiyoshi (Gonk). Also hilarious is that the mother is the only one in that family that actually speaks, while Sumiyoshi, his father, and his adorable little sister Canal all "speak" the same way.
- In InuYasha, Hiten and Manten's parents were both demons, but their father was a very human-like and extremely rather good looking demon while the mother was quite the Gonk, having a reptilian/toadish appearance with, in Manten's own words, "thinning hair". Manten inherited the mom's looks and Hiten looked like the Hot Dad, which gave Manten quite the inferiority complex.
- Change 123 gives us Kousukegawa's mom and dad. Dad is basically Kousukegawa aged up a few years, and given a good dose of Bishounen and glasses. His mom on the other hand is short, squat, and plain looking.
- In YuYu Hakusho, this MIGHT eventually be the case for Hiei and Mukuro.
- Takeo's parents in My Love Story!!. His mother is more of a gonk than his father, though she's not portrayed in a negative manner (much like Takeo himself), while Takeo's father is handsome and produces Bishie Sparkles (though he's not bishonen).
- Jack Kirby's Galactic Bounty Hunters, where Tyr looks like a Mr. Olympia contestant but his fiancée is fat, smelly, and very ugly. To be fair, they're aliens and from the way he acts she seems to be attractive by the standards of his race.
Films — Animated
Films — Live-Action
- The loving relationship between Wilbur and Edna Turnblad in Hairspray. Especially in the movie musical, with Christopher Walken and a cross-dressing John Travolta singing and dancing together in "You're Timeless to Me". A smaller example includes Tracy (a short, dumpy girl) and Link (Zac Efron).
- High School High: Mr. Clark took after his mother (who looks exactly like Jon Lovitz).
- Robin Hood: Men in Tights: This becomes the Sheriff of Rottingham's fate, after cutting a deal with the Witch to save his life; he reluctantly agrees to marry her in exchange for a magic pill.
- She-Devil: The failure of such a relationship drives the plot. In it, a man played by Ed Begley, Jr. is married to - and later cheats on and abandons - his wife, played by Roseanne Barr, who then seeks revenge. It's stated that he was trapped into marrying her after getting her pregnant in high school.
- Rafael and Lourdes from the Spanish film Crimen Ferpecto.
- Four Weddings and a Funeral ends with Scarlett, a plain looking woman with regrettable fashion sense, marrying tall, good-looking Chester.
- In The Hudsucker Proxy, Sidney Mussburger introduces his overweight, ugly wife to Barnes. Granted, the Mussburgers are an aging couple, but Sidney is played by Paul Newman.
- While not ugly, this is mentioned by Bill Clinton to Hillary in the biopic The Special Relationship regarding Tony Blair and his wife.
- Muriel from Muriel's Wedding being ugly is YMMV (one can say she's a BBW whose effort at presentation falls flat), but Citizenship Marriage husband David is a stunner.
- In A Brother's Price, breathtakingly handsome Jerin acquires one wife who has scars all over her face and upper body, a sight which disgusted her ex-lover so much that she left her. As sororal polygyny is the norm, not all of his wives are ugly, but this one is. Would have been played even straighter if he had had to marry the Brindle sisters, all of whom he thinks "look like horses".
- In Dragon Bones, Garranon, the favourite (i.e. mistress) of the king, is a very handsome man who looks a lot younger than his thirty years. He is married to a woman who is "no beauty". To everyone's surprise, they really love each other - Garranon may or may not be bi, but he hates the king, and only prostitutes himself in that way to protect his loved ones.
- In Harry Potter, it is established that the late Merope Gaunt was "no beauty" and got her handsome Muggle husband Tom Riddle by feeding him love potions. When she stopped drugging him, he fled the relationship, she fell victim to Death by Childbirth, and their child went to an orphanage where he grew up to become Voldemort.
- Used in The Obsidian Trilogy by Mercedes Lackey. Idalia, while certainly a beautiful human, has an elf pining for her. Then, at the end of the series, it's subverted, when she's reincarnated as an elf, though it's acceptable because this is the only way both would find long-term - by elven standards - happiness.
- Semi-used with Kellen and Vestakia—the fact that she looks like a Demon may repel others in-universe, but the reader is more likely to see her as a Cute Monster Girl.
- In Fairest, Aza, who receives rude stares and comments about her appearance and is implied to be descended from gnomes, has a handsome prince fall in love with her.
- Ron and Sarah in Russell Banks's short story "Sarah Cole: A Type of Love Story".
- In A Long Way from Chicago, this seems to be the opinion of some of the townswomen in regards to FDR marrying Eleanor Roosevelt. One can't believe someone so handsome settled for a woman so plain, while another speculated that it was because she was a good cook, as "kissing don't last".
- In Deep Secret, Maree, despite being fat, smudgy, and whiny of voice, had a rather attractive boyfriend before the story proper began, and later ends up with Rupert, who's rather handsome (if not the most handsome fellow in the story; that'd be Andrew) and has a fondness for leather jackets.
- In "Gone with the Wind", Melanie Hamilton is described as plain and homely by everyone who encounters her, and she marries Ashley Wilkes, whose good looks are expounded upon more than once by the narrative and the main character, Scarlett O'Hara.
- The Tamír Triad, sort-of sort-of-not prequel to the Nightrunner series by Lynn Flewelling features Prince Korin and his second wife Nalia - he is dashing, dark haired and tall (and a weak willed drunkard and beginning to show the family madness at that point) while she is described as plain looking at best (and by people who actually know her and see how kind, intelligent, gentle and utterly miserable the poor girl is) and outright ugly at worst, mostly due to her fleeting chin and the wine flaw on her face. Her life gets better. Tamír and her squire/childhood/friend/later husband Ki may or may not be an example. Ki is dashing. Tamír herself is not very much on the side of typical feminine beauty, shows very sharp features and she herself describes herself as rather plain. However, she has a lot of charisma, a keen mind, a strong will and is very compassionate, which is what draws people to her. And she's definitely far from ugly.
- Rizzoli & Isles: Literal plain Jane snags the gorgeous FBI agent Gabriel Dean.
- Belisarius Series has Rana Sanga and his wife. Rana Sanga is tall, handsome, broad-shouldered, widely considered the epitome of Rajput manhood and one of the half dozen best generals and personal combatants in the world. Lady Sanga is a short, pudgy, plain-looking woman whose hair was completely grey before her thirtieth birthday. Needless to say, Rana Sanga loves his wife more than anything in the world and turns into a tongue-tied teenager in her presence.
- The Conquerors Saga: Lada is ugly and has no illusions about it; Mehmed is described to be extremely handsome. In addition, being the sultan Mehmed has access to a harem full of incredibly beautiful women and a beautiful wife, whom he despises, but prefers Lada—he would love to sleep with and marry her, though she's having none of it.
- Married... with Children with Jefferson and Marcy D'Arcy, the Bundys' neighbors. Amanda (Marcy) Bearse was hardly ugly, but the joke was that she was a "chicken", a scrawny woman with no feminine features, and Jefferson was her trophy husband. She especially counts if you go by the same standards in Ugly Guy, Hot Wife, since like everyone else on the show, she had some glaring personality problems that did nothing to help her Hollywood Homely appearance.
- Rae's (rather frumpy) mum in My Mad Fat Diary lives with Karim, who is younger and fitter than her.
- Glee: Lauren, a fat girl (not Hollywood Pudgy, she's actually pretty fat) goes out with the super-hot, super-popular jock, Puck.
- Miranda constantly makes jokes about Miranda Hart being masculine, overweight and very, very tall. Yet she gets attention from quite a few very handsome men, especially Gary, her main Love Interest. However, it should be noted that Miranda Hart writes it herself, and there are a few real-life men who consider her attractive.
- Amen. Plain Jane Christmas Cake Thelma sees her wildest dreams realized when she snags the handsome Reverend Reuben Gregory - and before getting together with him, dates a decent amount of equally good-looking men, despite constantly wailing about her lack of a social life.
- On the Hong Kong television drama Only You, one of the clients that employs the services of the Only You wedding agency is an extremely handsome and wealthy playboy and his fiancee, a short, frumpy, and very homely microbiologist. She's insecure about the wedding because she feels that she's way out of his league since his model ex-girlfriend re-appeared and attempted to break them up. The story ends on a heartwarming note when he makes it clear that he genuinely loves his fiancee, because when he became one of the many afflicted by the SARS epidemic, she was the only one who treated him like a normal person, especially since said ex-girlfriend and the people he thought were his friends had abandoned him when he fell ill. He fell in love with her smart and kind personality, which made him reevaluate his perspective on people and not judging them by their looks, and a new life purpose in devoting his inheritance to philanthropy and supporting her scientific work.
- Days of Our Lives featured hunky doctor Craig and his considerably overweight wife Nancy, whom he absolutely adored.
- Crazy Courtney, a homely young woman with glasses, a crooked overbite with braces, and grandmotherly clothing is seen scaring away Josh Peck's character from his seat at the movie theater, it's then revealed she did it for the handsome, blond boyfriend of hers where they then say her catchphrase "Ma ha!"
- Two and a Half Men: Walden (Ashton Kutcher)'s ex-wife is less attractive than he is, with characters wondering what it is about her that draws attractive, successful men.
- Jokingly recommended in Jimmy Soul's 1963 hit, "If You Wanna Be Happy":
"If you wanna be happy for the rest of your life
Never make a pretty woman your wife
So from my personal point of view
Get an ugly girl to marry you"
- According to Warcraft, particularly Warcraft: The Roleplaying Game, the origin of the centaurs can be traced to the union of Zaetar (son of Cenarius, an attractive Night Elf/Stag centaur) and Princess Theradras, who would be pretty gonky even if she wasn't several times larger than him and built like the Venus of Willendorf with four arms and three faces.
- An example shows up with two background characters in Wurr—namely, the big fat hellhound and her leggy, elegant mate. Also a case of Tiny Guy, Huge Girl.
- Gravity Falls has a story where an ugly old witch tries to blackmail Stan into kissing her- instead, Mabel offers to give her a "Love Makeover" so she can get a guy of her own. She ends up... still ugly, but less terrifying, and in the end she is last seen with a handsome young rock climber who had been climbing by her cave.
- The Scotsman from Samurai Jack is married, and it's initially presented as Ugly Guy, Hot Wife; he's a hairy, burly warrior with British Teeth and a machine gun for a pegleg, and describes his wife as a paragon of beauty. Upon meeting her, it turns out the Scotsman's Wife is bigger, uglier, and meaner than he is by a fair margin, and he's nothing but a puddle of mush around her.
- In one Treehouse of Horror episode of The Simpsons, the ugly evil witch who holds Bart and Lisa captive claims that she has a boyfriend named George Cauldron, but the kids don't believe her. After Homer defeats the witch by stuffing her in the oven, her handsome boyfriend George Cauldron comes to her house, wondering where she is for their date.
- In the post-movie Spongebob Squarepants episode Banned in Bikini Bottom, we're given a stuffy, uptight elderly lady whose husband turns out to be the young, muscular, ridiculously humanlike Chief of Police. It's implied he married her for her cooking, which is odd considering she literally hates anything "fun and delicious," leading a whole community against it.
- Wallflower Tango, a German animated short, is about a woman with baggy eyes, a pointy nose, sagging breasts and deep laugh lines finally finds her chance at love when she catches a tall dark male burglar with a barrel chest and square jaw trying to steal her diamond.