I got an SOS yesterday from an exasperated wingman who was having a hard time winging for his newly single friend. The solution? Turn the tables on him.

“My friend has taken to ask me to ‘wingman”‘for him. I’m not the best wingman, but I initiate conversations for him anyway, but then he just stands there silently, or worse, uses a really cheesy pick-up line, and chicks are like ‘wtf.’ It’s really embarrassing and I feel creepy.”-Kyle, San Diego

Wow, sucks for you, Kyle!

No, really, that actually sucks for you. Here are some tips to make your winging a less painful experience for both you and your friend. (Otherwise, you’re just going to have to stop going to bars with him.)

Make HIM Wingman For YOU

Clearly, your friend needs some practice talking to women. But when he’s trying to pick up girls for himself, there’s a lot of pressure.

But if you ask him to wingman for you, he has to man up and break the ice himself–after all, you’ve done it for him countless times. So while he thinks he’s doing you a favor by chatting up girls, he’s actually practicing talking to women and refining his approach in a relatively low-stakes situation.

Give Him A Pep Talk

The poor kid obviously feels really awkward about this, so the most important thing you can do for him (and for yourself!) is to talk him up. Remind him that he’s awesome and fun to hang out with — definitely a better catch than most of the other guys in the bar.

If he feels relaxed and good about himself, it will make all the difference in the world when it comes to wingmaning.

Tell Him The Truth

Okay, his pick-up lines suck: you gotta tell him. You’re doing him a favor, really. (And speaking as a woman, you’re doing ME a favor, too.) If you’ve done the pep talk right, he’ll hopefully feel less reliant on a cheesy line, anyway.

Get Him Talking

It sucks to go through all the effort of initiating conversation with a girl, only to have your friend stand there silently. I asked Thomas Edwards, The Professional Wingman, for advice on how to wingman for a cold fish.

“The best thing you can do to open him up and get him talking is by asking him a direct, open-ended question for him to answer in the group. Make sure the question is something he’ll be comfortable with — better if it’s something he’s passionate about. Hopefully, he’ll give a good enough answer that will spark follow-up questions.”

Hook and Float

When you approach a girl, your entire objective is to make this couple hook–click, talk, hit it off–and then, most importantly, float. How can you tell if a couple floats? You extricate yourself from the situation as soon as possible by going to the bathroom, going to the bar, making a phone call, whatever. When you come back, is your friend still talking to the girl? You’ve got a floater! Is he sitting there awkwardly by himself? Sinker. Reel him in and go on to the next one.

You GOT this, Kyle! And your friend’s got this! Just remember, your first goal is to make him relaxed–and then make sure you’re relaxed. It makes all the difference in the world when it comes to approaching girls.

Good luck!

Filed Under:
Tweet