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A very common trope (in both Real Life and fiction) is the Ugly Guy, Hot Wife pairing. This is mostly because society's standards for female beauty are far higher than that for men, and women are often thought of as loving people on the inside, while men love women for their bodies and sexual wiles. Or it can be for another very good reason.
However, as rare as it may be, the inversion does in fact exist. While it's nowhere near as common, sometimes a totally hot hunk will end up with a Gonk of a girl. This usually plays on previous misconceptions of men and women's stances on love. Maybe the man has some ulterior motive. Maybe the girl managed to force him into such a relationship. Or maybe, just maybe, they really are in love.
This is not a YMMV trope; this is when the woman is clearly ugly, fat, skinny, or very visually displeasing in some way, while the man is incredibly attractive. Don't put down an example where "the guy is kind of good looking and the girl is kinda ugly, I guess".
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.
- 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.
- Gleefully used in the film Hairspray and its subsequent adaptations, where plump Tracy Turnblad wins over her teen idol classmate Link Larkin, who loves her no matter what she weighs.
- Which of course mirrors the loving relationship between Wilbur and Edna Turnblad. Especially in the movie musical, with Christopher Walken and John Travolta singing and dancing together in "You're Timeless to Me".
- High School High: Mr. Clark took after his mother (who looks exactly like John 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; where 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.
- Deep Secret: Maree is fat and dumpy, with frizzy hair, a droopy nose, and what's described as a very annoying voice. Rupert still falls hard and fast for her, and they too get married.
- It's not specifically stated that Rupert is hot, though.
- In Harry Potter, it is established that the late Merope Gaunt was "no beauty" and got her handsome Muggle husband by feeding him love potions. When the potions ran out, he fled the relationship, she died, 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.
- 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.
- In Gossip Girl, Dorota's husband Vanya is much more attractive than she is.
- Glee: Lauren, a fat girl (not Hollywood Pudgy, she's actually pretty fat) goes out with the super-hot, super-popular jock, Puck.
- The British sitcom The Vicar of Dibley sees plump Dawn French paired with tall, dark and brooding Richard Armitage. granted, she's the protagonist, and it was only in the season finale, but still. In Real Life, Dawn French was married to Lenny Henry. The show played a little with the issue. Her significant weight gain and eventual loss was even made part of the storyline. So this can depend on which episode you watch.
- 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.
- The Drew Carey Show: Mimi is large, unattractive, and doesn't do herself any favors with her make-up and clothes, yet, she doesn't seem to have many problems in the romance department.
- Days of Our Lives paired the handsome Dr. Craig Wesley with his considerably overweight wife--who he absolutely adored, defying many soap conventions in one fell swoop--happy marriages are rarely seen even with soaps model couples, so for this pair to be genuinely Happily Married really stood out. It probably helped that she was more of a Big Beautiful Woman rather than outright ugly, but the casting of a plus-size actress is rarely, if ever seen on soaps, unless for the purpose of a social issue storyline instead of simply choosing the best actress for the job.
- 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.
- On The Simpsons, the overweight and gravelly-voiced chain smoker Selma Bouvier dated and eventually married handsome actor Troy McLure. Though it didn't last, since it was ultimately a sham marriage meant to clean up Troy's reputation and get him better movie roles.
- Homely Meg Griffin has had several good-looking boyfriends over the course of Family Guy.
- Shelley Marsh and her messy hair, constant scowl, and over the top headgear have had a few cute boyfriends on South Park. Likewise, the overweight beehive-sporting and cranky Sheila Broflovski married the handsome and slender lawyer Gerald.
- Stan once dreamed up a love connection between ugly bus driver Mrs. Crabtree and a handsome trucker, which is odd considering his parents are both fairly decent-looking people. Maybe he believes this trope should be more commonplace.