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Anime and Manga
- In the hentai manga Slut Girl, Sayoko cons Satoru out of a lot of money. When he learns he's been conned he is so distraught that Sayoko takes pity on him and they have sex. But she is so impressed by his sexual stamina that they end up becoming Friends with Benefits.
- Yunoshin from the first arc of Ooku was known for this. The only son of a middle-class (at best) samurai household in Tokugawa-era Edo generations after an endemic man-killing plague took root in Japan; he is hopelessly in love with his longtime neighbor O-nobu, would sooner clean sewers than sell his services (despite having the looks, health, and bloodlines to command a decent 'stud fee'), and frequently tries to get unattractive, dirt-poor women with child just for the asking.
- G-rated pity marriage version, Doraemon, has Shizuka marrying Nobita because she feels that he cannot even survive without someone taking care of him. He used the time machine to go to the future, knowing that his future self is ill on bed and Shizuka trapped in a blizzard on top of a mountain, the primary school Nobita used tools of Doraemon and transformed into an adult version and took what he thinks is needed to save Shizuka. His clothing selection is of course not enough to withstand the cold, food cans without can opener, etc.
- In Empire State, Sara describes a date with a very unattractive man that ended with the two of them making out, partly because she felt sorry for him and partly because she didn't want him to think she was shallow.
Sara: But I felt so bad for him, Jimmy. He looked so sad. I guess I just didn't want to treat him the same way every other woman does. ... Long story short, Brent calls the next day for a second date, but my guilt had been assuaged by that point so I broke it off.
Jimmy: What a tease.
Sara: Whatever, dude. That make-out session probably got him through the rest of his thirties. He should be happy overall.
- In the notorious Sins Past story arc, Spider-Man's late girlfriend Gwen Stacey was revealed to have gotten pregnant after pity sex with Norman Osborn aka the Green Goblin. Editor-in-chief Joe Quesada thought this more acceptable than the original plot, which would have made Peter Parker the father of Gwen's twins.
- A variation occurs between Rogue and Magneto in the aftermath of the Age of X storyline when Rogue becomes torn between her feelings for Gambit and Magneto. Gambit states that she has to be ready for him for good before he could be with her again, and that he would be waiting for her when she is ready. After Rogue confronts Magneto about his past, he has a change of heart and tells her that becoming involved with him was a bad idea and that she should return to Gambit. However, Rogue has a change of heart of her own and decides to go with her feelings for one night of passion with Magneto, nothing more, noting:
"Most people want the things they know are gonna turn out to be bad for them."
- In Watchmen, Dr. Manhattan is in the middle of foreplay with Laurie when she suddenly feels a second pair of hands. He's doubled himself to attempt Three-Way Sex with her but it just freaks her out. Then she discovers that a third Dr. Manhattan is out in the main room still working on his project, infuriating her enough at what she calls "a pity fuck" that she breaks up with him and storms out.
- Zig-Zagged in The Life of David Gale. When Constance reveals she's dying of leukemia, David asks if she has any regrets. She tells him she would have had more sex. When he asks how many partners she's had, she thinks, then holds up four fingers. He asks if she wants to "complete the hand." Her response is an incredulous "A pity lay?" He then tells her it wouldn't be pity. Not quite Sex for Solace, either. David seems to genuinely care for Constance, although she doesn't seem to be all that attracted to him. Perhaps the pity is on her part, as he's just been divorced and fired.
- In the Vorkosigan Saga, Miles spends a year on Beta Colony at age 15. He has hopes for unlimited possibilities for sex, but finds that half of those interested (not many) are good Samaritans, and found that he "did not care to be an object of charity".
- Averted in Stranger in a Strange Land by Robert A. Heinlein. Jubal Harshaw believes that any of his three secretaries would probably have sex with him out of pity, but he himself is too proud to accept such charity.
- A Song of Ice and Fire: Averted with Sansa. She is fully aware that her total rejection on their wedding night is pretty much killing Tyrion, since it's a confirmation of one of his biggest fears, that his disability means that no woman will ever be attracted to him of her own free will. She feels very bad for him... which just makes the prospect of sleeping with him even less attractive. Even that is subverted in that we see from his perspective that he's actually relieved to have the excuse not to sleep with her, since he finds the circumstances of their marriage and her young age distasteful.
Live Action TV
- Game of Thrones: Inverted when Tyrion takes pity on Sansa by not having sex that would require exercising his Marital Rape License. This is as much out of his own revulsion at the situation as anything; he sees her as a child and has no more sexual interest in her than she does in him.
- In Smallville, done rather ambiguously from Chloe to Davis in "Eternal". A lot of it is non-verbal and is pretty much open for interpretation.
- In Community, Professor Slater first agreed to sleep with Jeff because he made himself seem pathetic, begging and pleading enough until she finally said yes. Subverted in that it never happened in that episode, and instead they first slept together after dating conventionally.
- Subverted in All My Children. This was Krystal's excuse for sleeping with Tad- emphasis on excuse, since she did have feelings for him.
- On Reno 911!, Dangle threw Trudy a "pity fuck". Jonesy did the same for Dangle once, too.
- Happens on the first episode of Friends with Benefits after Aaron gets dumped and Riley feels sorry for him.
- In Soap Jody has turned Carol down multiple times due to his homosexuality. When they're on holiday together, as friends, she starts crying and as he comforts her, they end up having sex.
- Better Off Ted: When Veronica was promoted to management, there was another employee with the same last name up for the same promotion, and a typo in the memo made it unclear which of them had been promoted. A few years later she meets the other employee again and finds out that his life since then had gone completely down the toilet, so she starts dating him out of guilt. She finally brings herself to dump him when Ted finds another memo proving that the promotion really was meant for her.
- Cabbage Head from The Kids in the Hall "Hey – I'm the KING of the mercy fuck!"
- Happens in an episode of season 3 of Skins, where JJ gets a pity fuck from the school lesbian no less.
- In Battlestar Galactica (2003), Felix Gaeta, who is days away from starting a mutiny aboard the Galactica, has a very hostile conversation with Starbuck in the mess hall. He notes that the illegal tribunal which nearly executed him for alleged treason earlier in the series was largely comprised of covert Cylons, one of them being Starbuck's own husband. As she walks out of the room, he uses this trope as a way to taunt her.
Starbuck: And if you were wondering... I will definately hit a cripple. That goes for anyone else. [walks off]
Gaeta: So I guess a pity frak is out of the question then?
- Glee has Rachel lose her virginity to Finn after he fails to get a football scholarship.
- Subverted in one episode of M*A*S*H, where a nurse who is about to be discharged is depressed because she's "never had anyone to care for her"; even her fiancé has only written once during the war. After the other nurses give an ultimatum to the men at the camp, saying they won't go near them unless someone spends the night with her, they draw lots; as fate would have it, Hawkeye draws the short straw. Unfortunately for both of them, this turns into a disaster, as she's so clumsy that she only manages to hurt him, badly. In the end, neither can go through with it, and Hawkeye simply gives her a kiss before she leaves.
- Discussed on The Big Bang Theory: After Penny gives Howard a pretty harsh "The Reason You Suck" Speech, he disappears into his bedroom for days. Finally, she resents and goes to talk to him. After he tries to put the moves on him, she punches him. When the others express concern, Howard gleefully says "The way I see it, I'm halfway to Pity Sex."
- Dork Tower tries to put a positive spin on this, in this strip drawn immediately after the Alyssa Bereznak debacle.
Matt: Dude is gonna get more sympathy nookie from cute geek girls than any human has the right to have.
Ken: He's been dealt the Beta Black Lotus of canoodling, yes ...
- In Ménage à 3:
- At one point, DiDi seeks to deflower Gary, who is a hopeless virgin. Various mishaps prevent her from doing so until Zii explains to her that she shouldn't, because Gary would associate sex with being pathetic. (Some readers assume that, consciously or not, Zii also does this because she wants Didi for herself — but of course, she doesn't say that.)
- Much later, new character Peggy offers DiDi sex out of pity for that fact that the latter has never had an orgasm. (They go ahead, but even Peggy can't solve DiDi's problem.) Pedants who know the comic may comment that nobody could ever have sex with DiDi just out of pity, though, and Peggy acknowledges her superhuman appeal.
- In this Sequential Art strip, Pip somehow ends up having pity sex with Kat's disgraced schoolyard rival Hilary.
- On American Dad!, Hayley needs a favor from her brother Steve. The price is admitting that Steve might one day get a long-time female friend to have "awkward pity sex" with him once.
- Lana has sex with Pam after taking pity on her in the first season finale of Archer.
- In Futurama Zapp, who fancies himself quite the ladies' man, first tries to charm Leela into sleeping with him, but since Zapp can't tell the difference between charm and sleaze, Leela just flat out rejects him almost immediately. This causes Zapp to break down crying about how pathetic and lonely he really is, causing Leela to ultimately sleep with him because she feels sorry for him. The same episode suggests that Zapp frequently does this intentionally to make women sleep with him, though the episode seems to suggest this is the first time it actually worked (with a woman).
- In Drawn Together Xandir, who is Camp Gay, "tosses a mercy-fuck" to Hollywood Pudgy Toot. He clearly didn't enjoy it.
- In an episode of The Simpsons, Barney's high school sweetheart returns to Springfield, and she is a successful journalist. Barney ends up saving her from peril by picking her up in his helicopter, after which he asks her if she might be willing to give him another chance. She answers that while she doesn't see any chance that the two of them can get together again, she is willing to give him a half hour of pity sex while he flies the helicopter.
By Proxy Examples
- Many of the gags in The 40-Year-Old Virgin revolve around Andy's friends misguided attempts to get him laid, including taking him speed-dating and hiring a prostitute who turns out to be a transvestite.
- Subverted (or maybe zig-zagged) in A Song of Ice and Fire. Tyrion's first sexual experience is with a woman who seems to just love him for who he is. Then it turned out that his brother Jaime hired a prostitute to play the part of Tyrion's loving girlfriend. Then it turned out that that was a lie Tywin forced Jaime to tell Tyrion — the woman wasn't a prostitute and really did just love Tyrion for himself.
- In Devdas after learning that he cannot be with Paro anymore, the titular character's friend introduces him to a High-Class Call Girl named Chandramukhi, in an attempt to cheer him up.
Live Action TV
- In The Big Bang Theory, Leonard and Raj hire a prostitute for Howard on a trip to Las Vegas that happens right after Leslie Winkle breaks up with him, though any sex that might ensue is glossed over.
- The pity sex by proxy happens in Boston Public; a romantically starved character discovers that his hot new girlfriend who actually seems to get him is in fact a prostitute hired by his wealthy brother. He didn't react well. (The 'girlfriend' was under the impression that the man already knew that he was getting "the girlfriend experience" and broke character at the wrong time.)
- The other cops hire a hooker for Renko's birthday in Hill Street Blues, and he was pissed when he caught on.
- In Family Guy episode, "Peter-Assment", Peter is forced to have sex with his boss Angela when she says she will commit suicide if he doesn't. When his friends confront him on cheating on Lois, he reveals he had Mort Goldman hiding in his pants.