The Matchmaker lives to get people together. They'd love nothing more than two 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 Incompatible Orientation. Maybe the two have so much in common that they'd rather be with someone else. Whatever the case, The Matchmaker 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.
Matchmaker Crush could be a reason why the couple doesn't work out. Thinks Like a Romance Novel could be another cause of this, as relationship aren't always this straightforward. If The Matchmaker is a Shipper with an Agenda, this failure might cause other problems if their motives are exposed. A Bad Date could either be the cause of or result in this trope.
Note: This is a Spoilered Rotten trope, that means that EVERY SINGLE EXAMPLE on this list is a spoiler by default and most of them will be unmarked.
- Naruto and Sakura are mentioned in I Am NOT Going Through Puberty Again! 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.
- Despicable Me 2: 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 Tranquilizer Dart to get Gru out of it.
- Set It Up: Harper and Charlie, beleaguered assistants 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.
- In Where Is The Nophelet?, this drives the plot. Ladies' man Gena tries to find a girlfriend for his Confirmed Bachelor 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 Matchmaker Crush on one of the women he found for his cousin, and his own wife arrives and puts a stop to it. 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 "Where is the nophelet?", and the girl is delighted because she was too shy to talk to him first.
- 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.
- In Female General and Eldest Princess, after Lin Wangyue gains a noble title, her house becomes besieged by professional matchmakers who want to set up "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.
- 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 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.
- When Annie starts dating Vaughn, both Jeff and Britta are disgusted. They plan to break the two up by encouraging Troy, who 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.
- 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 live out the sitcom cliche of having two dates at the same time. This results in the two girls getting hurt when they find out the truth.
- 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 looked like Abed only white.
- The Fresh Prince of Bel-Air had Vivian mention that she was once a matchmaker in college and she managed to get many couples married. However when Phillip stated at all the couples separated within five years, Vivian replied, "I just get them to the altar, after that they're on their own".
- Home Improvement: 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.
- How I Met Your Mother: 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, who Ted still has feeling for. In fact, he tries to get back together with her in the series finale after his wife dies.
- Roseanne: Roseanne sets up Jackie with Fred. The whole relationship ends badly. But not before it ended with pregnancy, marriage, cheating and divorce.
- Suburgatory: In one episode, Tessa notices a new boy checking out the jocks at the school. She 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.
- Will & Grace: 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.
- 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 realizes he doesn't like this other girl because she has no personality of her own and ends up getting back together with Jade.
- Changeling: The Lost: The Crimson Weavers are fae entities who are obsessed with the concept of "soul mates" and can mystically bind couples with a literal Red String of Fate. However, they have no clue what people actually like in each other, so those pairings are usually unfulfilling, and many go insane or kill their partners to escape their alleged "One True Love".
- Questionable Content: 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 tells Claire off for manipulating and publicly embarrassing them both.
Claire: W-wait! That's not how it was supposed to go!Clinton: It certainly went.
- The Gravity Falls episode "The Love God" has Mabel try to cure Robbie of his depression by stealing a Love Potion from a visiting Love God 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 Thompson who manages to convince the group to stay together by deliberately humiliating himself in public, while Robbie and Tambry stay together as a couple.
- In The Loud House episode "Teachers' Union", Lincoln tries to 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.
- In season 2 of Wander over Yonder, Wander, upon discovering that 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, but in the special musical episode "My Fair Hatey", she makes it perfectly clear in her Villain Song "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.