Two heads are better than one, as the old saying goes, and it can apply to courtship as easily as anything else. A common strategy is for a character to enlist a friend to assist him in his romantic endeavors. This "wingman" can build the character up as a sort of romantic hype man, offer advice, impartial feedback, and moral support, and run interference to distract friends of the Love Interest who might otherwise serve as walking Moment Killers. The fact that the wingman may wind up experiencing romantic success with such friends serves as an important fringe benefit. Can sometimes overlap with Expectation Lowerer when the wingman is meant to contrast their friend's good traits with their own bad ones, although for obvious reasons few wingmen do this intentionally.
As being a wingman can be seen as a subordinate position akin to a sidekick, there can sometimes be conflict over who is wingman to whom, or whose "turn" it is to act as wingman. On the other hand, Happily Married characters often enjoy acting as wingmen for their single friends as a way of vicariously recapturing some of the enjoyment of single life.
As the name implies, wingmen are traditionally male and assist male friends. In modern works, however, it is increasingly common for female characters to employ female wingmen or "wingwomen." In addition to the other functions of a wingman, such wingwomen are also sometimes asked to help deflect the attentions of undesirable suitors who are disinclined to take "no" for an answer. This can sometimes bring them into conflict with the suitor's wingman, who is tasked with distracting them. It can also sometimes bring them into conflict with the friend they are tasked with assisting, if the friend finds herself inclined to leave with a suitor that the wingwoman considers unworthy of her friend's attentions.
Men also sometimes enlist female wingmen with whom they are Just Friends. This has the advantage of what is called "social proof" or "preselection," the theory that some women perceive a man in the company of another attractive woman as more attractive himself. A common variant is for a straight man to work with a lesbian wingwoman, with the understanding that if a prospective paramour turns out to be a lesbian as well, the roles will switch and the man will assist the woman in wooing her.
Male wingmen assisting straight female characters are less common; the Gay Best Friend often offers romantic advice, but seldom offers the "in the field" support of a true wingman, perhaps because men are likely to perceive the presence of another man as a rival. The opposite— a Fag Hag winging for the Gay Best Friend— is sometimes attempted, but more often she acts as The Matchmaker instead. Gay characters acting as wingmen for other gay characters are also uncommon in fiction, perhaps because few works that are not explicitly gay-focused have more than one gay character.
Another common variation is to enlist a baby or animal to put the Casanova (or would-be Casanova) in a favorable light and serve as an easy topic of light conversation. For these, see the subtropes Pick Up Babes With Babes and Animal Chick Magnet. Like its subtropes, this trope is Truth in Television and is often seen in Real Life. Less often seen in Real Life is Playing Cyrano: a wingman putting words directly into a friend's mouth.
The slang term "wingman" comes from the fellow who guards the back of an Ace Pilot in combat, which is its own, otherwise-unrelated trope: Wingman. Compare The Matchmaker, who helps (or attempts to help) multiple parties find love as opposed to focusing on just one close friend.
- Kaguya-sama: Love Is War: Kaguya appoints herself to this role after finding out about Ishigami's crush on Tsubame, as she hopes that him winning her affection would be good for his self confidence. Given that this is Kaguya, her help involves forcing him to study more and encouraging Tsubame to turn down any other potential boyfriends as harshly as possible.
- My Love Story!!: Sunakawa plays this role to his best friend Takeo. Since Takeo is an Idiot Hero, Suna has to make Yamato confess her feelings to him several times without her noticing so Takeo could get her love through his thick skull. And it works. After the two got together, Takeo would often ask Suna for romantic advices to improve his relationship with Yamato or make her happy overall.
- 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.
- Undefeated Bahamut Chronicle has a side story in which minor character Huey asks Lux to introduce him to girls. This completely fails as all of the girls that Huey asks to be introduced to are already interested in Lux.
- 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 vice-versa, as their targets never overlap.
- Ted occasionally returns the favor for Barney, albeit not always willingly. In season three Marshall points out that according to Barney's Bro Code Ted may actually be a better wingman than Barney is.
- 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!"
- In an episode of Series/Friends Rachel is attracted to a new guy at work and asks Joey to take him out and befriend him. They meet a lot of women, which alarms Rachel ans she tells Joey to stop. He complains that he never had a real wingman before, and had to make do with Chandler. He says this in front of Chandler.
- Magnus of The Adventure Zone: Balance tutors Carey in carpentry to make a present for a friend in return for rogue lessons, but he intuits the gift will be for Killian, her girlfriend, and also crafts a lovely ring which he knowingly suggests Killian might like.
- 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 The credits of the episode even label her as "Ultimate Wingman".