Raj: You help me run my game.
Sheldon: Okay. What is your game?
Raj: When I lie through my teeth to a woman, you nod and agree.
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.
- 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.
- In MARRIAGETOXIN, Gero decides to accept his role as the heir of his family's clan and find a mate he could produce an heir with to protect his lesbian sister from being forced into the role. Since Gero has No Social Skills, he enlists the help of Kinosaki, a marriage swindler, who not only introduces him to potential brides but also gives him tips on how to make a good impression (which Gero almost inevitably fails at).
- My Love Story!!: Since Takeo is an Idiot Hero, Suna makes Yamato loudly confess her feelings for him several times with Takeo nearby, just to ensure there was no mistake. And it works. After the two got together, Takeo would often ask Suna for romantic advice to improve his relationship with Yamato or make her happy overall.
- Uzaki-chan Wants to Hang Out!: Sasaki will occasionally try to play this part for Sakurai, actively trying to set up situations to get him together with Uzaki. Ami sometimes will help too, if not as frequently given that she prefers the "wait and see" approach.
- On Yu Gi Oh 5Ds, after saving an unconscious Aki (his best friend's love interest) from a collapsing building, Jack tells her parents to bring in Yusei to help bring her out of her coma (he's right). Considering how he teases Aki about being in love with Yusei next season, Jack knew exactly what he was doing.
- In Scarlet Lady, Nino acts as this for Adrien, as he attempts to ask Marinette on a date. At the same time, Marinette is doing this for Alya, who wants to ask Nino out on a date. So far, Marinette has done better than Nino.
- In The Super Mario Bros. Movie, Kamek helps Bowser try to court Peach despite being absolutely hopeless when it comes to this sort of thing. At one point, he dresses as Peach to help Bowser in a roleplay of what he's going to do when he proposes to Peach; later, when Bowser actually attempts the proposal, he lies to him that he's "doing great!" when his "love really makes a guy come out of his shell" pun doesn't work.
- 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 who 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.
- Tanghi Argentini: Andre has made himself out to be an expert tango dancer to a lady on the internet. He goes to his friend Franz for some emergency tango lessons, then brings Franz along for moral support when it's time to meet the lady for real at the tango club. In the end, the trope is subverted when it's revealed that Andre was looking to match Franz up with the woman all along.
- Expecting to Fall into Ruin, I Aim to Become a Blacksmith: Played with when Prince Arc asks Kururi for help wooing Iris. Kururi is only humoring Arc, The Friend Nobody Likes, because he's Crown Prince, and ends up insisting on payment. The help mostly consists of Kururi informing Arc about common sense.
- In the Last Herald-Mage Trilogy Medren thinks his uncle Vanyel and his roommate Stefan would be good together and plays a role somewhere between this and The Matchmaker. After meeting Van, Stefan becomes fully a Ladykiller in Love and is dismayed by Van's insistence that It's Not You, It's My Enemies. Medren tries to arrange for them to hook up several times without success; the two only become close at all when Stefan just tries being a friend, but Medren can tell they both want each other. Finally, when Van and Stefan go to visit Vanyel's family, Medren just tells them they're already a dedicated couple, meaning There Is Only One Bed.
- Trapped in a Dating Sim: The World of Otome Games is Tough for Mobs: Female variant mentioned above. Marie protects her friend Noelle from her Stalker with a Crush Loic, beating him up a few times, while also giving hints to Noelle's actual crush. The former ends up working a bit too well.
- 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.
- Daredevil (2015): In a flashback to when they met as college roommates, Foggy Nelson gushes about how handsome Matt Murdock is, causing him to be Mistaken for Gay before he clarifies that he's actually enthusiastic about Matt as a wingman for helping him meet a better class of girl. It helps that Matt is disabled, electing sympathy from prospective dates as well.
- 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 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 and 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.
- 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.
- In a season one episode of Haven, Jess shows up at the Haven PD, with a thinly veiled story about a prowler at her farm (a six-foot-seven tattooed prowler with a unibrow and a slingshot, no less) to get Nathan alone, but Nathan is so socially awkward he just doesn't get it. Audrey, his police partner, who has been sitting across the room increasingly appalled he's so Oblivious to Love, finally takes pity on him and arranges the date for him. And he's still clueless.
Audrey: Jess, I think Detective Wuornos needs to come by and conduct a safety review of your home. Say around eight?Jess: Great. I shot a deer so we're having venison. Maybe you can bring a nice bottle?Nathan: Of...wine.Audrey (exasperated): No, antacid.
- 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.
- 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.
- 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.
- 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.
- Final Fantasy XIV:
- In the Weaver quests, Redolent Rose subtly helps his friend and long-time customer Wawarukka score a date with the Lalafell's Uptown Girl crush, Kokomo. The main obstacle to Rose's efforts is how Wawarukka is a complete Rummage Sale Reject, forcing Rose to eventually go against Wawarukka's requests by dressing Wawarukka up in a proper suit to give him a shot at impressing Kokomo and her unapproving father. After the events of Endwalker, Rose is happy to report that Wawarukka and Kokomo are now Happily Married.
- In the sidequest, "Short on Courage", the Warrior agrees to accompany a lovelorn Dwarf and give him the courage to woo a Hume girl whom he's fallen in love with at first sight. But he's too shy to even try to ask her out, requesting the Warrior ask if she's unwed and if she'd be interested in dating a Dwarf. After she tells them that she's interested in a kind and generous soul, regardless of appearances, the Warrior can tell him this, inspiring the Dwarf to become more like the Warrior by taking to the road in hopes of becoming a man worthy of marrying her. In this case, the player can choose to subvert this by saying that the girl is interested in someone like them, shocking the Dwarf who didn't expect them to be a romantic rival.
- In the Endwalker Studium Deliveries, the Warrior is recruited to act as this for Hinageshi in hopes of getting Professor Tankin to realize her feelings for him since she Cannot Spit It Out. The Warrior even presides over the couple's Ceremony of Eternal Bonding in Searcher's Meet. As Hinageshi and Tankin kiss, the Warrior can be seen looking on with a satisfied smile on their face.
- Galaxy Angel: In Moonlit Lovers, Ranpha can occasionally play this part outside her own route. Most prominently with Vanilla, as the latter has trouble expressing her emotions and seems to have a difficult time grasping that she's in love with Tact.
- 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 convinces the guy who gets it, Sasan, to go meet Finley in person.
- 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.)
- 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 being too forward.
- 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.
- 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.
- Questionable Content: Shortly before they became a couple, Faye and Bubbles discussed their relationship status.
Faye: If you ever need a wing-lady, I'm your girl.
Bubbles: That turn of phrase concerns me. If your love live requires close air support, something has gone very wrong.
- 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.
- The most shocking pairing of this kind you could never imagine occurs in the SpongeBob SquarePants episode "Love that Squid" — a very rare example of one of the main male characters (in this case, Squidward) going out with a female. Not only does SpongeBob secure Squidward's date with her when the latter is too nervous to talk but Squidward begs SpongeBob to help him prepare for the date.
- 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".