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- At the party scene of Dumb and Dumber, Harry attempts to play up Lloyd's good qualities to Mary. However, his attempt goes so poorly that it's Harry that ends up on a date with Mary instead. Harry tells Lloyd that he hooked him up with Mary anyway, and it's off to the races.
- The 1996 film Swingers helped popularize the slang version of the word "wingman." In it, several friends take main character Mike out on the town to help rebuild his self-confidence and enhance his romantic prospects after a bad breakup. Initially, the wingmen find more success than Mike, but by the end he has met a promising romantic prospect played by Heather Graham.
- In How I Met Your Mother, Barney acts as main character Ted's wingman, largely by introducing him to women with a game he calls "Have You Met Ted?" (which consists entirely of Barney approaching an attractive woman, introducing himself, and asking "Have you met Ted?" before walking away, leaving Ted to carry the conversation whether he wanted to or not). He also does this for his gay brother, and vise-versa, as their ‘targets’ never overlap.
- One episode of The Girl's Guide To Depravity is centered around Amy enlisting Sam and her friends to serve as "wing women" as she visits a lesbian bar, despite the fact that the other girls are all straight.
- The aptly named Person of Interest episode "Wingman" has as its POI a man who started doing this professionally after he set up a friend with his wife. Fusco goes undercover as a client to guard him.
- In one episode of Home Improvement, Tim agrees to be Al's wingman when they go to a bar. Hilarity Ensues after Al manages to hit it off with a woman since her friend falls for Tim. Tim's wife Jill is amused by all of this. Tim is not.
- Flight of the Conchords: Brett asks Jemaine to be his romantic wingman, "like in Top Gun!" Jemaine snaps, "Stop comparing everything to Top Gun!"
Stand Up Comedy
- In a sketch about nightclubs, mating rituals and "going out on the pull", Oop North comic Mike Harding observes that women come in twos for mutual support. He described this as "The Harding Theory Of Women," observing that there is always a good-looking one and a "tug" pulled along in her wake. He speculates that this is because the good-looking one isn't threatened by competition, and the "tug" is in a position to capitalize on any spares she drops off. Harding also adds that he goes out with so many tugs he is nicknamed the Queen Mary.
- In The Taming of the Shrew, Baptista wants to marry off his daughter Katherine (the eponymous shrew) before allowing anyone to pursue his younger daughter Bianca. So Bianca's suitors enlist the help of Petruchio to woo Katherine, which he does with much enthusiasm.
- In Mass Effect 3: Citadel, Shepard (of either gender) has the opportunity to play this to a non-romanced Garrus, mostly by helping him pluck up his courage and intervening when inevitably he puts his foot in his mouth. (Amusingly, if she's romancing Garrus, Shepard encounters the same turian woman with a Death Glare.)
- In The Legend of Zelda: Breath of the Wild, the Zora girl Finley has been regularly sending a Message in a Bottle (or rather, in a barrel) downriver in the hopes that she'll find true love with whatever "prince" finds it. Link can follow the barrel as it goes downstream and convince the guy who gets it, Sasan, to go meet Finley in-person.
- In Ménage à 3, Zii offers to act as "wing girl" to the virginal Gary. The joke turns out to be that she keeps getting distracted and doesn't really have much idea how to go about helping him, and he ends up getting laid more or less regardless of her efforts. However, he does credit her with giving him some essential confidence, just by telling him that he's not beyond hope.
- In Homestuck, Roxy tries to help her "bffsy" Jane win over the guy she has a crush on — even though Roxy sort of has a crush on the same guy.
- Furry Experience: Luke, in the "Knock, Knock" arc, begins acting as one for Hunter, who keeps shooting himself in the foot in his attempts to get close to Cat. He acts as a go-between for them, helping Cat see him in a more positive light, and keeping Hunter from beeing too forward.
- Their Story: Mophead is one to Sun Jing in the "straight man for lesbian" variant, and does a surprisingly good job at it, given their normal choice of interaction is to dick around with each other.
- On Archer, Sterling's buddy Lucas Troy used to serve as his wingman back when he still worked for ISIS.
- In the Family Guy episode "Mr. Griffin Goes to Washington'', Peter is given a cushy new job that brings with it fringe benefits for his family, including an ugly wing-girl hired by the company to stand next to Meg and make her look better by comparison. It is comically effective.
- In the Steven Universe episode "Last One Out of Beach City", Amethyst serves as this to Pearl when she realizes Pearl has a crush on a biker chick they encounter en route to a rock concert who looks like Rose Quartz.