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Anime and Manga
- Happens early on Lovely Complex too.
- In Ranma ½, Ranma goes on a date with Ukyo so he can spy on Akane's date with Ryoga. Ryoga and Ranma inevitably end up fighting, and both transformed into their curse forms.
- At the start of Marmalade Boy, a play on this is the explanation behind the current relationships of the main characters' parents, though the truth is more complicated.
- In episode 28 of Jewelpet Sunshine, Ruby ropes Tour into going on one of these with Kanon and Mikage so she can spy on what they do.
- The four main characters in Tonari no Kashiwagi-san go out on a double date to an amusement park. Only Kotone actually fails to realise it's a date at all.
- The movie Keeping the Faith, although one of the couples on the double date are in fact the other character's best friends, only pretending to be on a date, and only there for moral support. Bonus points for one of the best friends being a priest.
- When Harry Met Sally... has a flagship use of this trope, including "Bob" and "Dana" getting together.
- The plot of Drinking Buddies is set off by a cabin trip that turns out to be one of these. During the trip, Jill and Chris (Alice and Carlos, respectively) wind up kissing, while the UST between their actual paramours Luke and Kate is the primary source of drama throughout the movie.
- Heathers : Heather McNamara convinces Veronica to go on a double date with herself, Ram, and Kurt. It ends badly.
Live Action TV
- 7th Heaven: Mary wants to go out with Robbie but her parents forbid it because they don't trust him. She asks if she can go out if it is a double date with Robbie's brother and her own sister Lucy also present. Her parents agree to that, and she drags along an unmotivated Lucy, while Robbie does the same with his brother. Ironically, Lucy and Robbie's brother turn out to like each other, and at the end of the date both couples are making out with each other next to each other.
- Smallville: "Escape" has an accidental and really awkward one with Lois/Clark and Chloe/Oliver, since Lois and Clark had no idea that that Chloe and Ollie were seeing one another...before running into them wearing bathrobes together when they accidentally book the same bed and breakfast. The next morning, the four of them end up sitting a the breakfast table, still looking hilariously awkward. Ollie amusingly tried to break the tension: "Look...little jellies."
- Castle does this in "The Third Man"; though he and Beckett are more interested in talking about the case at hand than each other, it does end up the same: They step out to solve the case, and their dates hook up.
- The Cheers episodes "Save the Last Dance For Me" and "Diane's Perfect Date".
- Happens on Noah's Arc, with Dre (who is with Noah's ex Wade) inviting Noah over for dinner. Unbeknownst to Noah, this is to set him up with Dre's friend Quincy. Though there's clear Unresolved Sexual Tension between Wade and Noah, in later episodes Noah actually does start to fall for Quincy.
- On one episode of The Brady Bunch, Greg's Girl of the Week agrees to go out with him only if he can find a date for her out-of-town visiting cousin. However, Greg can't convince any of his friends to double-date with him because, last time anyone saw her, the cousin had pigtails and braces. So Greg convinces Peter to do it (with difficulty), and he has Peter wear a bad fake moustache to make him look older. Of course, 1. the cousin has lost the pigtails and braces and is now super hot (Greg clearly thinks she's hotter than his own date), and 2. the two girls see right through Peter's Paper-Thin Disguise. So they conspire to both ignore Greg and give all their attention to Peter.
- The song "Tokyo Summer Session" by Honey Works features a triple date, where the three main couples go to watch a fireworks festival. They didn't actually go together, and the pairs didn't meet up until the very end, but the entire song does showcase the different dynamics between the couples — from Natsuki and Yuu's colourful but strong relationship, Sota and Akari's slowly but surely budding romance, and the UST between Mio and Haruki that's still hindering the progress of their relationship.
- Rhythm Heaven Fever has a mini game called Double Date, set at a schoolyard. One couple is human, and the other is a pair of weasels. To keep everyone happy, the player needs to kick away stray sports balls that are headed for the weasel couple.
- El Goonish Shive: Tedd and Grace with Ellen and Nanase. This led to Tedd and Ellen finally making progress in their friendship, though they may disagree on whether it's a preexisting friendship or a new one, due to Ellen being an Opposite-Sex Clone of Tedd's best friend Elliot... it's complicated.
- In Kevin & Kell, post-divorce Martha and George go through a period of taking dates to the same restaurant at the same time. At least once, this results in their dates leaving with each other while George and Martha sulk.
- Kim Possible and Ron double dated with Shego and Mr. Barkin. Barkin and the kids felt awkward together, so the double date was a disaster.
- Amy and Kif with Zapp and Leela in "Amazon Women in the Mood", though Leela only came as a favor to Amy, since she hates Zapp.
- Depicted above is from "The Butterjunk Effect", where Amy and Kif double date with Fry and Leela.
- In "Put Your Head On My Shoulders" with Amy and her new flame and an old woman who Bender picked out for Fry from his matchmaking business. It should be noted that Fry and Amy were only double dating because Fry's head was currently attached to Amy's neck.