This is when somebody tries to ruin someone else's romantic relationship or marriage. There are various reasons someone might do this. One of the most common is that the saboteur is in love with one of the people in the relationship, and is willing to stoop pretty low to "correct" this situation. (In extreme cases, they may even try to Murder the Hypotenuse.) Alternatively, it could be that they just want Revenge for something, or that they want to free up one of the parties for a bit of gold digging, or that they're simply bitter that someone else is so happy and they're not. Sometimes, they may even be acting from a genuine, well-intentioned, and possibly even accurate belief that their friend has made a poor choice or should have chosen someone else. The range of techniques available to a relationship saboteur is similarly varied. Lying is popular - you just need to make one half of the relationship look bad, such as by fabricating evidence of an affair or trying to make them flunk a Fidelity Test. It could be as simple as giving deliberately lousy relationship advice. If the relationship is fairly new, being a deliberate Moment Killer might be an option, and might prompt the saboteur to follow the targets on dates. See also Break Up Demand for a different method of achieving the same goal. If a character simply makes their dislike of the pairing known, it's probably just a Shipping Torpedo. Contrast Shipper on Deck, where someone is trying to create a relationship rather than destroy one.
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- In one commercial, one teenage boy forces his younger brother upstairs so he can spend time with his girlfriend. The younger brother then uses the TV to show the girlfriend a slideshow of pictures that indicate he's cheating on her.
- In the backstory of Saiunkoku Monogatari, Kou Reishin and his friend Houju were both interested in the same woman. Reishin sabotaged Houju's relationship with her by forging a letter from her to Houju saying she couldn't bear to be with a man so much more beautiful than herself. As a result, Houju started wearing masks all the time and calling himself "Kijin," meaning "weirdo," and Reishin married the girl.
- Skuld in Ah! My Goddess, who takes her Big Sister Worship towards Belldandy a bit too far and won't stand for anyone, particularly lowly mortal Keiichi, getting too close to her. She frequently sets up booby traps (mostly involving Stuff Blowing Up) to prevent their relationship from progressing. It is hinted a few times, though, that she's acting out not because she's jealous of Keiichi for taking Belldandy's attention, but that she's jealous of Belldandy for getting Keiichi's love.
- Makie from Futari Ecchi does that at every opportunity to the main character couple. I.e., she leaves false lipstick marks on Makoto's shirt or calls him in the middle of a date with his wife Yura.
- Happens more than once in Marmalade Boy, with the most notorious perpetrators being Kei Tsuchiya (who grabs Miki's medallion/bracelet and gives it to Yuu saying she threw it away; Yuu is Genre Savvy enough to not buy it, but he and Miki still almost break up due to stress.) and Ginny Golding (who lies to Miki by telling her she was Yuu's "other woman" as a prank; this causes the already distraught Miki to break off her and Yuu's Long Distance Relationship.)
- Naruto, after finding out that Sakura doesn't care for him at all while he's disguised as Sasuke, is forced to retreat to the restroom because he drank spoiled milk in the morning. While on the toilet, he plans on returning to Sakura, still disguised as Sasuke and acting like a jerk in order to make her hate him. By the time he gets out, though, Sasuke has already escaped his bonds, and coldly told Sakura that he finds her annoying (although the way the scene is presented leads viewers to initially think that it was Naruto in disguise carrying out his plan).
- Ranma ½: Ryoga, Shampoo, Ukyo, Kodachi, and other characters all try to sabatoge Ranma and Akane's engagement at some point or other.
- Ranma and Akane team up in the manga to thwart the possibility of Hinako and Soun marrying.
- Chihaya of Servant × Service is dead set on preventing Yutaka and Lucy getting together. Some of Lucy's hesitation on dating Yutaka originates from Chihaya making him sound more devious than he really is. This is mostly because she wants to cosplay Lucy and erroneously believes that so does he.
- In the anime of Sailor Moon, Lita is jealous that her crush, Andy, has a girlfriend. Upon finding out that the girlfriend is tempted to accept a job abroad which would separate her from Andy for a long period of time, Lita nicely sits down and has a talk with her, trying to convince her to take the job. She ends the talk with the suggestion that Andy and the girlfriend could very well pick up where they left off, before lampshading to herself how terrible she is at sabotaging relationships.
- At the end of Frank Miller's Daredevil, a grieving Matt Murdock had pressured his rather fragile girlfriend Heather Glenn into agreeing to marry him, which was literally driving her to drink. Believing that no good could come of this for anyone, Matt's partner Foggy and his ex the Black Widow created forged notes telling each partner that the other one wanted to break it off and never see them again. The immediate consequences were never shown, but a few years later Heather committed suicide.
- Lana Lang attempted this occasionally when her jealousy of Clark and Lois' marriage got the best of her. In one instance she tried to convince Clark that Lois was a bad wife and left her panties in the Kents' bed in a fit of jealous anger when Clark refused to be swayed by her arguments.
- In one of the stories of the Facing The Future Series, Danny's enemies unsuccessfully tried to this to Danny and Sam.
- In another story, Nocturne nearly pulled this trope off by sealing away their memories of each other, only to be thwarted by The Power of Love.
- Ponyville Goes to the... Dragons??: Applejack warns Rarity not to attempt this Trope when she learns Spike has started a relationship with Ember, telling her about how she knew about Spike's affection for her yet did nothing about it when she had the chance, and stating that she'll prefer being sent to the moon compaired to what AJ will do to her if she tries anything. Still doesn't stop her from giving an anonymous 'tip' about there being vicious dragons in Ponyville to the Canterlot Royal Guards...
- In My Best Friends Wedding, Julianne tries to derail the upcoming marriage of a guy who had promised to marry her if they were both still single at a certain age. It fails, epically.
- Pretty much the entire plot of the film Saving Silverman.
- Both Balraj's sister Kiran and Darcy's mother try very hard to keep Jaya and Lalita very far away from Balraj and Darcy in Bride and Prejudice.
- Sherlock Holmes went out of his way to try to get Dr. Watson to not get engaged to Mary since he wanted to keep him for himself. He insulted Mary with a deduction and he paid a fortune teller to plant seeds of doubt into Watson's head. He eventually did give his consent.
- In Plan B, Bruno's "Plan B" to make his ex-girlfriend Laura and her new boyfriend Pablo break up is to seduce Pablo and drive him away from her. It works, but by then it's not Laura he wants to be with.
- In Mulan 2, Mushu tries to break up Mulan and Shang to save his job. When Mulan finds out, she gets pissed. Fortunately, Mushu makes amends.
- This is Peggy's plan in The Best Years of Our Lives: she declares that she's going to break up the unhappy marriage between Fred and Marie. It's not really her fault the marriage falls apart, but she does get Fred in the end.
- In Wicker Park, Alex does this to Matthew and Lisa's relationship as we learn via flashbacks. She never delivered that one letter that would have explained Lisa's sudden departure to Matthew.
- In Short Cuts, Stormy Weathers fires torpedos at his soon-to-be ex-wife Betty's relationship with Gene Shepard as part of his revenge against her. He first leaves his son Chad with her instead of taking him for the evening per their custody agreement, so that she is forced to take Chad on her date with Gene. Then, when Gene calls her at home after his suspicions that she is having yet another relationship are roused by her flimsy cover story regarding why she can't spend the weekend with him, Stormy answers the phone and pretends to yell at Betty to put some panties on before hanging up.
- Pride and Prejudice:
- Mr. Darcy doesn't believe that Jane Bennet holds any particular feelings for Mr. Bingley, not realizing that Jane is too shy and reserved to express her love openly in a way that would stand out from how nice she already is to everyone. Because of this, and because he (not entirely inaccurately) sees Jane's mother and sisters as appalling Gold Diggers, Darcy prevents Bingley and Jane from meeting in London and encourages Bingley to break off his courtship of Jane.
- At least Darcy is motivated by genuine concern for his friend's happiness, and regrets his actions when Elizabeth makes it clear that Jane really does love Bingley. On the other hand, Bingley's sisters rudely rebuff Jane when she tries to visit them in London and participate in the sabotage because they look down on the Bennets, and because Caroline wants to marry Darcy and thinks that will be more likely to happen if Bingley were to marry Darcy's sister Georgiana.
- Dr. Austin Sloper in Washington Square goes out of his way to ruin his daughter Catherine and Morris's relationship, culminating in taking her on a trip to Europe for a full year to test the strength of their affection. His reasoning is that he is convinced that Morris is nothing more than a Gold Digger after his family's fortune. He turns out to be right.
- In The Zombie Knight, Geoffry's grandfather did this to his mother. Primarily, it was to create a suitable host for an aberration, bet he does admit that he also thought it was funny.
Live Action TV
- In the sixth season of House, House decides to try to break up Cuddy and Lucas after deciding that he might just be interested in the former.
- In Sugar Rush, the efforts of Sugar to sabotage the relationship between Saint and Kim rather indicate that she's not being honest about having no interest in the latter.
- In The Big Bang Theory, Evil Wil Wheaton sabotages Leonard and Penny's relationship in order to win a bowling game!
- On Gossip Girl, this is Blair's MO. And not just for own ex-boyfriends - she's perfectly happy to break up any new relationships that might make Serena unhappy too. Chuck, as well, loves to mess with any relationships that would a) stop Blair being with him or b) distract Nate from their friendship. And Jenny does this occasionally. And Vanessa - oh, screw it, let's just say Gossip Girl is built around this trope and leave it at that, okay?
- On How I Met Your Mother Lily has done this to Ted six times, each time because she thinks the girl Ted's dating is a bad fit for their group of friends. Methods range from planting a woman's earring in Ted's bed so his girlfriend thinks he's cheating on her, to planting a Creed CD in the girlfriend's apartment so that Ted becomes disgusted with her, to dressing up in the girlfriend's Darth Vader costume, pretending to be her, and telling Ted they should see other people.
- Later on, Lily is called upon to break Barney and Robin up, but a sudden bout of Complexity Addiction almost does her in.
- Happened all the time on Rome.
- This is pretty much Diana Fowley's job during season six and seven of The X-Files. She's working for the Syndicate to lure Mulder, but whether her true aim in breaking up Mulder and Scully is professional or personal (she's Mulder's ex-partner and may or may not be his ex-wife) is up to interpretation. She plays off Mulder's previous trust in her, and almost succeeds in breaking them up. To the delight of many a shipper, she is killed off in the early parts of season seven.
- The season 4 finale of iCarly had a revelation that Sam likes Freddie. It's quite possible that her actions in iSaved Your Life, where she completely fucked up Carly and Freddie's newly formed relationship by planting seeds of doubt in Freddie's mind was a subconscious desire to sabotage the relationship to keep Freddie away from Carly.
- In pretty much any episode of Glee in which Finn Hudson is dating somebody not named Rachel Berry, you'll find Rachel trying some form of this, by means including: staging singing lessons that are intended to turn into something a lot less innocent; dramatic changes of appearance (fortunately Kurt was onto her and ensured it didn't work); informing Finn that his girlfriend is pregnant by another boy; duetting with other boys (particularly if it's the boy who got his first girlfriend pregnant) to make Finn jealous; and encouraging him to distrust his girlfriend and spy on the boy a blind item in the school newspaper implies she's cheating with in company with, you guessed it, Rachel Berry. Every single one of these backfires on her in some way. You'd think she'd have caught on by now, but no such luck...
- Mary of Downton Abbey tells her sister Edith's suitor that Edith was looking for an "old bore" as revenge for Edith's spreading Mary's Dark Secret.
- Friends: Phoebe does this to Monica and Chandler a few times, whether accidental or deliberate, through playing on Chandler's fears as an Insecure Love Interest. She tells him Monica saw her old boyfriend Richard and later introduces Monica's 'soulmate' right in front of him. (And AFTER they're married). Thanks to Monica and Chandler's strong relationship nothing sticks and the only result is several heartwarming scenes of Monica promising Chandler is the love of her life and she's not interested in anyone else. It's not clear if Phoebe is just being her usual Cloud Cuckoo Lander self, or a Green-Eyed Monster, that they're happy and she isn't.
- In Merlin, Morgana tries and fails to break up Gwen and Arthur in "Queen of Hearts" but succeeds masterfully (though temporarily) in "Lancelot du Lac."
- In Tokimeki Memorial 2, Knight Templar Big Brother Kaoru "Sou-Banchou" Ichimonji will constantly try to do this in Akane's storyline. Resolved to prevent any boy to hurt her little sister's feelings, and also fearing to lose her (who's his sole family) if she ever hooks with a guy, he will sic at you his underlings, then will fight you in person, will barge in the scene if he feels you're too close from her, and in Memories Ringing On, will even go as far as trying to sabotage your wedding ceremony preparations with her by threatening the assembly hall's clerk of obstruction of business! Said sister is not very pleased by her brother's antics, and constantly resolves them with a Megaton Punch.
- One of the selling points on the back of the Mister Mosquito boxart.
- In Captain Morgane and the Golden Turtle, Chief Chemi'n doesn't want his cousin Tana to hook up with Chief Bajari, and so convinces the clueless-about-love Bajari that any "weird feelings" Bajari gets when thinking about Tana are an illness caused by Tana putting a curse on him. Morgane sets him right.
- In General Protection Fault, Trudy steals Ki's stuffed animal "Mr. Pookel" and leaves it where Nick will find it so that he'll learn her screen name. He's upset with her for not telling him in order to test his loyalty, but ultimately forgives her.
- Homestuck has a variant skewed a bit by the nature of troll romance. Basically, trolls have four romantic quadrants - "genuine love", "Morality Pet", "mediation between two others" and "mutually destructive hatelust" - and you're generally expected to have relations with a given person confined to only one quadrant. As a result, at one point Casanova Wannabe Eridan attempted to sabotage Feferi and Sollux's "genuine love" romance by trying to make Feferi mediate between himself and Sollux, which would push them out of their preferred quadrant.
- The Simpsons once had Bart try to break up the relationship of his Precocious Crush (with the added motivation that the person she was going out with had bullied him).
- In an earlier episode, when his best friend Milhouse started 'dating' the new girl at school, he tipped off the girl's Overprotective Dad so Milhouse would hang out with him again. He ended up regretting it.
- In another episode, Milhouse's parents (who several seasons back had a nasty Toilet Seat Divorce) are getting back together. Which seems great at first, except that Milhouse starts to feel that they're ignoring him. He complains about this to Bart, and Bart sees a Teen Drama on TV wherein a girl angrily dumps her boyfriend because she found another girl's bra in his room. Bart steals one of Marge's bras and leaves it in the Van Houtens' bedroom. But because the bra had Marge's name sewn into it, it poses a threat to Homer and Marge's marriage as well. Homer and Marge reconcile over the fact that it was a big misunderstanding.
- King of the Hill: Peggy sabotages Lucky & Luann's relationship.
- Helga always fails at this in Hey Arnold!.
- My Dad The Rock Star has Quincy trying to break Willy and Alyssa up because he thinks that if they're together, they wouldn't want him hanging around getting in their way.
- Archer tries to get his ex back by manipulating recordings of her current boyfriend in order to make it look like he's cheating on her. She doesn't believe him, but still appreciates the effort.
- Archer's mom also purposely drives Lana closer to her boyfriend to get her away from Archer, because while Lana and Cyril are the Official Couple, she can see the Unresolved Sexual Tension between her and her son.
- And Archer's "Operation Something About I Rescue Lana and She Begs Me to Take Her Back, so Then Cyril Commits Suicide."
- Diaspro in Winx Club is in love with and originally engaged to Prince Sky. However, Sky falls in love with Bloom and breaks up with Diaspro. Diaspro is still in love with Sky and tries to brainwash him with a love potion. When this fails, she turns to more conventional means such as not letting the two spend time together and feeding the two misinformation in an attempt to drive them apart. She's helped when Sky's father declares her his liaison, giving her some power over Sky.
- In the first season of Total Drama, believing they are forming an alliance that could threaten hers, Heather does this to Gwen and Trent. To make it worse, due to the misunderstanding, everyone votes Trent off.
- The Spectacular Spider-Man - Aunt May finds out that Peter might have a date with an older woman who isn't Mary Jane, and therefore tracks the woman down and pressures her into breaking it off. And she gets away with this.