Approaching the Person Together
Wing only for people who are roughly at your level. Don't try to wing for someone who is significantly less appealing than you. These are harsh words, but they are true. You and your friend should be pretty similar in terms of your attractiveness, your outgoing nature, and your general appeal. Otherwise, the people you meet are likely to latch on to you, and your buddy will feel even worse. This doesn't mean that your friend can't appeal to people just because they’re less attractive than you. But if they also lack charisma and flirting skills, while you're a smooth operator, then you won't have much luck.
Give your leader the first choice of people. That's what the wingman is for, right? If you're winging, it's either because you owe your friend one, because you're not single, or just because you want your friend to have a good time. That means you can't switch roles and take over engaging the person that your friend has their eye on. Learn how to read cues to tell which person your friend wants. You might even want to designate hand, eye, or verbal signals beforehand.
Let your friend take the lead. When you come up to a group, make it so they notice your friend first. Stand a bit behind and to the side of your leader — literally positioning yourself like a wing. Also try to replicate the leader’s attitude and body language — if they’re going for “super-friendly” or “super-chill,” follow suit. You don't have to look like a total dud during this process, of course — don’t make it seem like you’re hiding/lurking/cowering behind your buddy. Think of yourself as the Robin to their Batman.
Don’t initiate the conversation yourself. Let your friend make the introductions and start talking with the people, while you slowly make your way into the conversation. Otherwise, it won’t be clear who’s in charge. Remember that Batman always talks before Robin. If there is just one person, you can let your friend talk to them first and join in later. If there are two people, give your leader a few minutes to warm up to both of them before you join in.
Keep the target’s friend busy while your leader works. For the rest of the night, occupying the main target’s friend(s) is your primary goal. If it’s a group of two, spend your time focusing on the secondary person by distracting and keeping them busy. Try to pay as little attention as possible to the primary person, even if they seem interested in you. It's important that, once you figure out which person your friend wants, you stick to the other person from the beginning. If you try to switch off midway through, your targets will get confused.
Maintaining a Supporting Position
Provide interference if necessary. Think of yourself as part friend, part bodyguard. If other people come your way to horn in on the object of your friend's eye, it’s your job to get them out of the way without looking like a jerk. The more attractive and appealing the person of your friend’s advances is, the more you must be on the lookout for interlopers. Stave off interlopers by distracting them, getting in their way, or subtly annoying them until they buzz off.
Speak up and shut up at the right times. You should make the person group laugh here and there, reveal a bit about yourself, and keep the conversation flowing, but you shouldn't talk so much that you end up stealing the show. Your friend should be the one who does more of the talking, and you should bail them out when there's an awkward silence or when you can contribute something that makes your friend look good. Don't interrupt your friend when they’re talking unless you really have something to add. Otherwise, you'll make your friend look like a chump. If it does get a little quiet, don't say "Now this is awkward..." Just speak up and get the ball rolling again.
Don't get distracted. Maybe the most beautiful gal or guy you’ve ever seen just rolled in. Maybe your favorite team has gone into overtime with their biggest rival. Maybe your brother called, asking for a favor. That's all well and good, but not tonight, if you want to be a good wingman. You need laser focus on the task at hand — to help your friend go home with, or at least to get the number of, the person they’re interested in. Tell yourself that you're doing your friend a favor, and that you'll get your turn another day.
Don't get too intoxicated to be useful. This should go without saying, but this is a mistake wingmen are prone to making. So what if you're stuck talking to someone you don't really care about? If you drink too much, you will look like a fool and make your friend look like a fool by association. And who wants to go home with a fool? Pace yourself. Unless you’re both the designated wingman and designated driver, it’s fine to drink enough to keep near the pace of the group. But call it a night if you start to lose focus.
Stay in it for the long haul. Getting tired? Wanting to go home to play video games? Too bad. Tonight is not your night to make decisions. Unless you really have a pressing reason to go home or are having a particularly horrible time, you have to grin and bear it. As soon as you say you have to go home, the spell is over, and you will have ruined your friend's chances if they haven’t come close to closing the deal. If you really need to leave, give your friend some advance notice — maybe even by text — so they can come up with a plan for staying in touch with the person.
Mention if you’re in a relationship — eventually. If you approach two targets and announce that you have a boy/girlfriend within the first five minutes, they probably won't hang around to talk to you. But if you go two hours without mentioning this fact, then you'll look sketchy. Find a casual way to introduce your relationship status into the conversation, once you've gotten to know the person group a bit better. Many leaders prefer a wingman who’s in a relationship, since they’re less likely to try to steal the main person. Also, a wingman who smoothly lets it be known that they’re taken can help ensure that the main person will focus on the leader even more.
Ensuring Your Leader’s Success
Make your friend look good — but not too good. You might think that your goal as a wingman is to tell the target that your pal is the smartest, coolest, richest, and most talented person around. However, the target will quickly catch on to your game if you go down this path, so make your friend look good only if you can make it a part of the conversation naturally. This doesn't mean that you should put your friend down or make them look like a loser, though. That won't help, either, and you'll both end up looking foolish.
Keep your friend presentable. Let your buddy know if they spilled beer on their pants or have something stuck in their teeth. Also let them know if they’re getting too drunk and looking like a fool. If you want your friend to succeed, then you have to keep them looking good. Even if you're occupying the target’s friend, don't ignore your own friend completely; make sure they’re staying on track. If you do have to tell them that they spilled a drink on their shirt or that something about their appearance is off, try to be subtle about it. Setting up a series of signals beforehand might help.
Let your friend know if they have no chance. This is another key aspect of being a wingman. If you see them talking for a long time to someone who’s looking around the room or checking their phone every five seconds, you'll be doing your friend a favor by saying, "Hey, I think we should move on." Though their pride may be wounded, they'll thank you for not wasting the night. An hour is the maximum amount of time to wait. You can often figure out whether or not the target is warming up to your friend in as little as ten to fifteen minutes — and sometimes almost instantly. Remember — a good wingman has to make the tough decisions sometimes, even if they’re not popular in the moment.
Highlight connections between your friend and the target. Look for things that the two have in common, and try to help them find that common bond whenever you can. If the target mentions that they just took a trip to L.A., mention that your friend is from there (especially if they missed the comment). If you notice the target has a keychain with your pal’s favorite NFL team’s logo, tell them that your friend has season tickets. Look for opportunities to enhance the connection between your friend and the target. You can enhance the truth a bit, but don’t make it too much of a stretch. You can't force them to bond over something your friend really doesn’t know all that much about.
Break formation and depart when your work is done. At the end of the night, you should hang back and let your friend work their magic. If you have the target’s friend to occupy, you can move on somewhere else first so they feel more comfortable. If you've both been talking to a solo target, go to the bathroom or order another drink while your friend’s wrapping up. Get out of the way so your friend can get a phone number — or someone to take home. Make sure you have your own way of getting home if necessary. You don’t want to kill the mood by sharing their cab home. If it just doesn’t work out in the end, don't sweat it. You tried your best — and that’s all that can be asked of a wingman.
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