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1TheMatchmaker lives to get people together. They'd love nothing more than to watch a couple they've set up walk off into the sunset. However, things don't always work out how they've planned. Maybe they've misjudged the couple. Maybe the two had an IncompatibleOrientation. Maybe the two have so much in common that they'd rather [[OppositesAttract be with someone else]]. Whatever the case, TheMatchmaker has failed to bring them together. Reactions to this failure may vary. The matchmaker might just shrug it off or getting very angry, depending on their investment in the relationship. That's not even getting into how the couple themselves react to this meddling.
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3MatchmakerCrush could be a reason why the couple doesn't work out. ThinksLikeARomanceNovel could be another cause of this, as relationships aren't always this straightforward. If TheMatchmaker is a ShipperWithAnAgenda, this failure might cause other problems if their motives are exposed. A BadDate could either be the cause of or result in this trope.
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5'''''Note:''''' As this often comes as a surprise, expect spoilers!
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8!!Examples
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10[[foldercontrol]]
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12[[folder:Fan Works]]
13* Naruto and Sakura are mentioned in ''Fanfic/IAmNotGoingThroughPubertyAgain'' to have picked up the hobby of trying to pair their friends together. While this actually has resulted in a few happy couples (Choji/Karui and Kiba/Tamaki being among the listed examples), they only have a 1 in 12 success rate, and their attempt to pair Shino with Kiba's older sister Hana in particular resulted in millions of ryo in property damage on the first date.
14* Yang Dae-su decides to become a 'Love Doctor' in ''Fanfic/ThisIsAWildGameOfSurvival'' after seeing his classmate Ji-min look on sadly as his friend Gyeong-su and her friend Na-yeon become close, and tries to set up Ji-min and Gyeong-su... too bad she's actually an ArmoredClosetGay and really into Na-yeon. Not helping is that his attempts at matchmaking involve loudly asking a very short-tempered girl about orgasms, getting attacked by a crab, and tackling Gyeong-su. Additionally, when he learns that his best friend Woo-jin is bisexual and into their friend Joon-yeong, he tries locking them in a closet... except he does it so quickly, he ends up pushing someone wearing the same-colored shirt as Joon-yeong in with Woo-jin instead: Ji-min.
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17[[folder:Films -- Animation]]
18* ''WesternAnimation/DespicableMe2'': Jillian is constantly trying to set Gru up with women. He eventually goes on a date with her friend Shannon. However, the two have vastly different personalities. Not to mention, Shannon gets angry at the fact Gru is wearing a wig, as she thinks it means he's a "phony". It goes so poorly that Gru's love interest Lucy has to shoot Shannon with a TranquilizerDart to get Gru out of it.
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21[[folder:Films -- Live-Action]]
22* ''Film/SetItUp'': Harper and Charlie, {{beleaguered assistant}}s to two tough New York executives, conspire to set their bosses up to make their work life less stressful. Things get hairy when Harper and Charlie discover that Charlie's boss Rick is cheating on Harper's boss Kirsten with his ex. Eventually, Charlie personally sabotages Rick and Kirsten's relationship when he realizes that by allowing their relationship to continue, he is compromising his own ethics.
23* In ''Where Is The [[SdrawkcabAlias Nophelet]]?'', this drives the plot. Ladies' man Gena tries to find a girlfriend for his ConfirmedBachelor cousin Pavel, using the eponymous question as a pick-up line. However, due to Pavel's shyness, it only ends in huge embarrassments (such as Pavel running away during a game of spin-the-bottle). Finally, Gena develops a MatchmakerCrush on one of the women he found for his cousin, and his own wife arrives and puts a stop to it. [[spoiler:Subverted in the end. After Gena leaves the city, Pavel musters the courage to talk to a beautiful stranger he sees every day on the bus. He asks her "[[RunningGag Where is the nophelet?]]", and the girl is delighted because she was too shy to talk to him first]].
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26[[folder:Literature]]
27* ''Literature/DevilVenerableAlsoWantsToKnow'': Wenren E tries to matchmake Baili Qingmiao with Zhongli Qian to free her of her unhealthy obsession with He Wenzhao, but no romantic feelings arise between them and they become LikeBrotherAndSister instead. It probably didn't help that Wenren E is [[WhatIsThisThingYouCallLove so clueless about what romantic love even is]] that his conclusion after reading a book's description of love making you happy whenever your the person you love is happy was "if I infect two people who have never met each other before with parasites that force them to feel each other's emotions all the time, that will definitely make them fall in love!"
28* ''Literature/{{Emma}}'': Emma loves matchmaking, spending a good deal of the novel trying to set up the people around her with each other. Yet, the ''only'' time she's successful is when she sets up Miss Taylor and Mr. Weston; every other one is a failure.
29* In the first ''Literature/{{Evernight}}'' book, Bianca and Lucas subtly try setting up Bianca's friend Raquel with Lucas' friend and roommate Vic, including the four of them going out to lunch together. While Raquel and Vic don't dislike each other, it's clear they're ill-suited as a potential couple, having little in common. Raquel later playfully mocks Bianca's attempt to set her up with Vic; it also comes out that Raquel is a lesbian (with Raquel being surprised Bianca didn't figure it out sooner), so that just adds to the failed matchmaking.
30* In ''Literature/FemaleGeneralAndEldestPrincess'', after Lin Wangyue gains a noble title, her house becomes besieged by professional matchmakers who want to set up [[SweetPollyOliver "General Feixing"]] with a good wife. When she rejects them outright and instructs her servants to ignore them, the matchmaker guild takes offense and starts spreading unsavory rumors about her, which are only cleared when Wangyue lets slip that her heart already belongs to an Imperial Princess.
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33[[folder:Live-Action Television]]
34* ''Series/{{Blackish}}'': In one episode, Junior asks his sister Zoe if she can help set him up with a girl he likes. Zoe scoffs at this, finding the [[NoAccountingForTaste girl too nerdy]], and tries setting him up with a more attractive girl. It looks like she's successful at first, as Junior lands a date with this girl. Then he reveals the only reason the girl went out with him was so he would edit a video for her. Zoe is actually more upset about this than Junior because she took pride in her matchmaking skills.
35* ''Series/{{Community}}'':
36** When Annie starts dating Vaughn, both Jeff and Britta are disgusted. They plan to break the two up by encouraging Troy, whom Annie had a crush on, to pursue her. The thing is, Annie had gotten over her feelings for Troy, and his attempts to pursue her fell flat. This results in both Troy and Annie getting mad at Jeff and Britta. They do succeed in breaking up Annie and Vaughn, but it's only temporary.
37** In another episode, both Annie and Shirley try to set up Abed with girls. Abed doesn't tell his dates about the other as he wants to [[MetaGuy live out the sitcom cliche of]] [[TwoTimerDate having two dates at the same time]]. This results in the two girls getting hurt when they find out the truth.
38** In an early episode, the group discovers a picture of Abed with hearts drawn around him in a Spanish textbook. Excited to learn someone has a crush on Abed, the group pushed him to find the girl who drew it and ask her out. It turns out that the girl wasn't drawing a picture of Abed, but her boyfriend who [[IdenticalStranger looked like Abed]] [[PaletteSwap only white]].
39* ''Series/TheFreshPrinceOfBelAir'' had Vivian mention that she was once a matchmaker in college and she managed to get many couples married. However, when Phillip stated that all the couples separated within five years, Vivian replied, "I just get them to the altar, after that they're on their own".
40* ''Series/HomeImprovement'': In "Heavy Meddle," Jill decides to play matchmaker for her friend Karen with Tim's friend Dave. Several episodes later, Tim gets dragged into it when Dave cheats on Karen. They end up splitting for good.
41* ''Series/HowIMetYourMother'': Inverted. Ted learns that Lily has been sabotaging his relationships with women she doesn't think are right for him. One of these women is Robin, whom Ted still has feelings for. In fact, [[spoiler:he tries to get back together with her in the series finale after his wife dies.]]
42* ''Series/TheOfficeUS'': After Jim and Pam have their baby, an emotional Michael becomes convinced the two got together thanks to him and is inspired to matchmake the other employees in the office. He tries it with Kevin and Erin, and while Kevin is enthusiastic, Erin already likes Andy, so it doesn't work out.
43* ''Series/{{Roseanne}}'': Roseanne sets up Jackie with Fred. The whole relationship ends badly. But not before it ended with pregnancy, marriage, cheating, and divorce.
44* ''Series/{{Suburgatory}}'': In one episode, Tessa notices a new boy checking out the jocks at the school. She [[MistakenForGay assumes he's gay]] and tries setting him up with a jock she believes is in the closet. It turns out the new boy was actually an undercover cop who was investigating steroid use by student athletes. He believed Tessa was helping him with the investigation and ended up arresting the jock she tried setting him up with.
45* ''Series/WillAndGrace'': In the episode "Whose Mom Is It Anyway?" it is mentioned that Grace's mother Bobbi has a history of setting her up on incredibly embarrassing and disastrous dates. When Bobbi sets Will up with a guy named Andy, Grace thinks this will finally convince her what a poor matchmaker she is. However, this is subverted when Will and Andy hit it off and Grace starts fearing that her mother is giving up on her ever finding a match.
46* ''Series/{{Victorious}}'': When Tori notices a girl is interested in Beck, she tries to encourage him to date her. Beck doesn't want to because his ex Jade might be jealous. Tori's solution is to set Jade up with someone else. Unfortunately, the boy Tori tries to set Jade up with is terrified of her. Jade does end up giving Beck her blessing to date this other girl. However, Beck [[AllForNothing realizes he doesn't like]] this other girl because she has no personality of her own and ends up getting back together with Jade.
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50* ''TabletopGame/ChangelingTheLost'': The Crimson Weavers are [[TheFairFolk fae entities]] who are obsessed with the concept of "soul mates" and can mystically bind couples with a literal RedStringOfFate. However, they have no clue what actually makes real relationships work, so those pairings are usually unfulfilling, and many go insane or kill their alleged "OneTrueLove" to escape.
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54* ''Webcomic/NoEnd'': Cotton encourages Benny to act on his long-term crush on Jerry -- forcing Jerry to admit that he already knew and [[JustFriends isn't interested]], reveal that he ''is'' [[LoveTriangle interested in Cotton]], and ultimately leave the group until people's hurt feelings settle. Worse, Cotton had genuinely hoped the perpetually dour Benny could find some happiness, but was ''terrible'' at judging the situation.
55* ''Webcomic/QuestionableContent'': [[TheMatchmaker Claire]] tricks her brother Clinton into visiting his crush Emily at her workplace so he has no choice but to ask her out. She turns him down. Outside, he [[https://questionablecontent.net/view.php?comic=3208 tells Claire off]] for manipulating and publicly embarrassing them both.
56-->'''Claire:''' W-wait! That's not how it was supposed to go!\
57'''Clinton:''' It certainly ''went.''
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60[[folder:Western Animation]]
61* The ''WesternAnimation/GravityFalls'' episode "The Love God" has Mabel try to cure Robbie of his depression by stealing a LovePotion from a visiting {{Love God|dess}} to set him up with Tambry. This backfires horribly, as it causes Wendy's group of friends to break up: Wendy hates Tambry for dating her ex-boyfriend, while it turns out Nate had a crush on Tambry that he told Robbie about, and had promised he wouldn't try dating her until Nate asked her out first. Mabel desperately tries to fix it using an anti-love potion, but winds up making things worse and invokes Love God's wrath. In the end, it's [[ButtMonkey Thompson]] who manages to convince the group to stay together by [[FailureGambit deliberately humiliating himself in public]], while Robbie and Tambry stay together as a couple.
62* In ''WesternAnimation/TheLoudHouse'' episode "Teachers' Union", Lincoln tries to [[StudentsPlayingMatchmaker pair up Mrs. Johnson (his teacher) and Coach Pacowski]], but he inadvertently idealised Coach P too much by telling her that he travelled a lot (without realising those photos were actually of him at a golf course) and had a boat (when really he lived in a houseboat). This makes Mrs. Johnson sour and she breaks up with him.
63* Played with in ''WesternAnimation/MyLittlePonyFriendshipIsMagic'', where in one episode Sweetie Belle, Scootaloo, and Apple Bloom try to set up their teacher with Big Macintosh. When it doesn't work, they brew a love potion for them, which [[GoneHorriblyRight goes a little too well]] and they become SickeninglySweethearts. At the end, they break the spell and learn a valuable lesson about interfering in other people's relationships.
64* In season 2 of ''WesternAnimation/WanderOverYonder'', Wander, upon discovering that [[SamusIsAGirl Lord Dominator is a girl]], constantly tries to set her up with Lord Hater. However, he only succeeds in making ''Hater'' fall for Dominator. Not only is the love ''completely'' one-sided, [[spoiler:but in the special musical episode "My Fair Hatey", she makes it ''perfectly'' clear in her VillainSong "I'm the Bad Guy" that she doesn't want Wander's assistance or Hater's adulation and would much rather bring their galaxy to ruins for her amusement.]]
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