Alan and Barbara are in a relationship, but Alan knows something's wrong, to the point where he decides it's better to just end things. He could just sit Barbara down and tell her, "You know, this isn't working out. I don't think we should be together anymore."
But that would be too easy.
So Alan tries to get Barbara to break up with him first, usually by engaging in unattractive behavior.
Reasons for this vary. Alan might know the relationship has to end, but he doesn't want to be the bad guy, especially if what's turning him off could be seen as shallow or insignificant by others. He might genuinely want to spare Barbara's feelings, and figures that she won't be heartbroken if she's the one who initiates the breakup. He might realize that he's not the one she belongs with, and does this to make her see that. He might be afraid of what her father or big brother might do to him. Or if they're married, they might have a prenup that makes it desirable for Alan not to be the one to request a divorce.
Almost always backfires, especially if played for comedy. Success typically results in No, Really, It's Okay if Alan hasn't pissed off Barbara too much.
In more serious works, discovering this trope in action will result with the wannabe dumpee labeled a Dirty Coward. Unless it turns out that he's Dating Catwoman in which case the fear is justified.
Happens inReal Life, and let's leave it at that.
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Anime and Manga
Godai tried this with Kozue several times without success in Maison Ikkoku.
Ranma ½ had Ranma trying to do this to Ukyou in the "Secret Sauce" arc by pretending to be even more coarse and callous than he actually was. She saw right through his pathetic acting.
Karin: Karin can't get Dogged Nice Guy Winner to understand that she's not interested in him. So she tries going on a date with him and acting like a total demanding bitch so he will lose interest. It doesn't work.
Keroro Gunsou: When Karara started crushing on Tamama, he acts very crude and coarse, getting the others to back him up by talking about all his faults. ...This also doubled as Brutal Honesty, as he does have all the same flaws they were "lying" about, but he didn't realize that he was telling her exactly what was really wrong with him.
Yuno tries this in Mirai Nikki, since she comes to want Yukiteru to hate her.
Benio Hanamura from Haikarasan Ga Tooru deliberately screws up with her Yamato Nadeshiko training so her arranged fiancé Shinobu Iijuin and his family will put an end to their engagement. It fails since Shinobu himself is a Nice Guy and keeps forgiving everything... and she ends up falling for him as well.
In Melinda And Melinda, one of Woody Allen's worse movies, the plot is told twice, once as a comedy and once as a tragedy. In the comic version, Will Ferrell plays a husband who desperately wants to break up with his wife to run off with the eponymous Melinda, but can't think of an excuse to. He walks in, preparing to tell his wife that he was dumping her...only to find her in bed with another man. Will Ferrell immediately demands a divorce and leaves happier than he'd been the whole movie.
The Graduate: Benjamin, under orders from Mrs. Robinson, tries to get her daughter Elaine to lose interest in him by taking her to a strip club on a date.
A rather tragic version is mentioned in Dogma, when one of the Golden Claf boardmembers apparently got his girlfriend drunk at a party and arranged for another guy to sleep with her, just so he could dump her without himself looking bad for it. She ended up committing suicide over her "betrayal of trust".
This is also the plot of nearly every Jeeves and Wooster novel. Bertie is a... can't remember the word, start's with a p, but he's got this thing where he can never say "no" to a woman. It's French. Anyway, Jeeves usually ends up doing something amazing to solve both his problem and the problem of the week at the same time. Preux chevalier, that was it.
Harry: And speaking of getting shot of people, will you stop pretending to be asleep when Lavender comes to see you [in the hospital wing]? [..] If you don't want to go out with her anymore, just tell her.
Ron: Yeah...well...it's not that easy, is it?
Live Action TV
Done repeatedly on Seinfeld. Tactics included suggesting a threesome, cheating, nosepicking, smoking and asking for a prenuptial agreement (the last three were with the same woman). Sometimes it worked, but more often than not, it backfired.
Richard on Caroline in the City tried nosepicking, too. It backfired miserably when the intended dumpee became gleeful at the prospect that Richard was comfortable enough in their relationship not to hide his disgusting habits around her... and consequently felt no shame about now trotting out her disgusting habits.
Meredith thinks Derek is doing this at one stage in Grey's Anatomy, when he flirts with her sister. It turns out he does want her to dump him, but it's because she's always walking away from him and then coming back, and he loves her too much to leave her when she's a bitch to him. This is a bit rich, though - I mean, who had the secret wife here, huh?
One episode of My Name Is Earl had Earl get back together with a clingy girlfriend. After realising she was emotionally needy (and not wanting to tie her down too much), Earl tried to get her to stand up for herself by acting like a complete dick so she'd move on and find someone else. He resorts to having her find him in bed with another woman, which still doesn't get her sufficiently annoyed, before he talked to her about what he was doing.
In another episode, Catalina has entered into a Citizenship Marriage with Randy so she could leave Guadelatucky and go back to Camden. Randy has had a crush on this Spicy Latina all series long, and he is very excited about consummating the marriage. Catalina, however, finds Randy repulsive. So (on the advice of Joy), she makes herself purposely unappealing by not shaving her armpits, getting sweaty, rubbing onions and dead fish on herself, and not brushing her teeth...and making mention of Randy's parents having sex. It turns out that as repulsed as he was, Randy was the best lover she'd ever had! Be Careful What You Wish For
Drake does it in Drake & Josh, when he finds out his girlfriend is the daughter of his Sadist Teacher. Said teacher says she'll treat him even more harshly in class if he breaks up with her, so he tries to make her break up with him instead.
Niles Crane did this to get his second wife Mel to divorce him so he could finally get with Daphne, the love of his life. However, there's a twist: not wanting to suffer the social embarrassment of her husband leaving her for another woman a few days after marriage, Mel is the one who engineers the Please Dump Me ploy to make it appear that Niles is the worst husband ever and that she is the innocent, devoted wife who is driven to divorce. She blackmails Niles into compliance (promising a "quick, simple divorce" in return) and in true Springtime for Hitler fashion her attempts to make him look bad horribly backfire.
Believing that his female roommate is attracted to him, Joey on asks Ross and Chandler for advice on how to repel women (suggestions were explaining one's jokes, making rimshot noises, and talking about science.)
During one of Chandler's relationship crises, Phoebe accuses him of trying to do this. Joey then asks "You know about that?"
Salute Your Shorts had an episode where Budnick fell in love with Dina, and reformed his ways to go out with her. But because All Girls Want Bad Boys, Dina wasn't as attracted to him when he wasn't a rebel, and the other campers found the "new" Budnick even more obnoxious than the old one. To get their jerk back, Dina had to push him away.
In Wizards of Waverly Place, Alex does this to get rid of Dean, but it backfires when he wants to help her get herself together. Finally, she blurts out the truth and he agrees to dump her anyway.
In Misfits, Curtis tries this on his girlfriend Sam. Even though he’s the one doing the dumping, he has to do it in such a way that will make her furious rather than sad (for reasons too complex to go into – lets just say it involves defence mechanism superpowers and Time Travel). In his desperate attempts to provoke the desired reaction, he accuses her of having "weird tits" and "nasty snatch-gunk", and claims to be impotent, gay and terminally ill. None of it works. In the end, it’s Curtis trying to justify his actions with a quote from a Spiderman movie that makes her hate him and want to break up.
After drunkenly proposing to Dorothy in Men Behaving Badly, Gary tries to make her call it off with ridiculous conditions:
Subverted in the end, as it turns out Dorothy was just stringing him along (of course upon learning this, Gary gets offended and manages to argue his way into her wanting to marry him again).
This is the justification many caught-in-the-act suspects on Cheaters give when pressed about why they're cheating. Apparently, they don't want to really break up the relationship, but are fine spending lots of time pissing off their partner...
In The Vampire Diaries Caroline breaks up with Matt by starting a jealous argument about him talking to another girl, which she already knows that he hates.
Stand Up Comedy
Sam Kinison had an entire bit about this, though given his sense of humour, he suggests getting hooked on various hardcore drugs.
Subverted if the player romances Morrigan in Dragon Age: Origins. She does this, even going so far as to beg the player to say he doesn't love her, not because she doesn't have feelings for him, but because she's scared to death she might.
During her romance in Baldur's Gate II, Viconia spends a little while trying to make the player character hate her when she realizes she's not exactly wearing the pants in the relationship (and might be falling in love).
In Penny and Aggie, Karen advises Stan on what to say to drive Michelle away. However, he considers her advice—"Start ordering for her at restaurants. Ask...for a diet salad, and put a little emphasis on the word 'diet'"—too cruel even for the Jerkass he is at this point in the story.
For weeks after her return from Hollywood, during which she fell for, kissed and nearly slept with another girl, Sara delays telling Daphne it's over. When she notices Daphne glaring at Sara's best friend Penny over her aristocratic behaviour, Sara thinks, "Don't make a scene, Daph. Make a scene, Daph," suggesting that part of her longs for an excuse, that doesn't involve confessing her borderline-infidelity, to dump her. Some time later, when Daphne and her childhood best friend Fred (who's also gay) share a platonic kiss during a party game, Sara sports a noticeably jealous look, but denies feeling that way when Daphne calls her on it. When she does finally get up the nerve to break up with Daphne, Sara confesses that she had been "trying to send a clear signal" but decided not to throw a fit about the kiss because she realized she was being "a brat and a coward, waiting for an easy way out."
Alan from the webcomic Avalon drew this out for three years with Helène.
TV Go Home has Nathan Barley, who in one episode of his eponymous show "Cunt" tried to let his girlfriend down gently over a six month period, an endeavour which eventually results in his happy and lively girlfriend being sectioned (for non-Brits, hospitalised against her will under the Mental Health Act). The additional text from this entry makes absolutely no bones about the cruelty and selfishness of this.
Done in Sixteen, because he was her boss's son, and she didn't want to be fired. Doesn't work, but it winds up that the reason it doesn't work was because he also thought he'd get in trouble for dumping her.