How To Not Be The Worst Wingman


At your typical college party (if you can remember that far back), there was no reason for wingmen to exist, because alcohol did. When everyone’s guzzling great quantities of liquor, it’s less necessary for someone to convince you to throw your inhibitions to the wind, because they’re already long gone. At your average party, enough guys were there that when a newly created couple wanted to break off from the crowd, they could do so with ease.

Now that we’re regularly dealing with Post Grad Problems, wingmen are one of them. When faced with the awkward age/stage that comes before serious relationships/marriage, meeting up with friends is a precursor to penetration. This makes “dating” seem casual, and it gives you an easy escape route if things go rogue. It also means that unless your wing-people are feeling each other, they’re left to lurk.

The wingman’s purpose is simple: to guarantee that his buddy gets it in. However, most wingmen seem confused on how to be normal human beings, an easy feat for most people. Wingmen tend to fall into two categories: the creeper or the watcher. Both are equally awkward when you’re hoping to get to know someone better, because they’re either scaring your friends, staring at you, or both.

A wingman’s job should be easy. He’s really only there because it would be awkward/misconstrued as alcoholism to hang around bars alone. Or he’s there because meeting up with friends seems more casual than a one-on-one date, especially if it’s last minute. If a wingman is dedicated to his friend, he’ll provide possibly (probably) made-up compliments, while he prevents her friends from dissuading her from the situation. He’s there to make it look like the guy in question is socially adjusted enough to have friends, and not a Craigslist murderer.

Unlike college, you don’t have a million mutual friends to confirm that the guy you’re meeting up with doesn’t want to murder you and wear your skin as a suit. A wingman proves that he’s kept one guy around long enough without murdering him, which should make you feel safe.


The first type of wingman, the creeper, thinks that he’s going to get lucky Daft Punk-style because his buddy found a lady for the night. He doesn’t realize that just because your friend is hitting it off doesn’t mean you’re DTF (down to fall in love). This is especially true if the wingman isn’t as normal as your friend’s gentleman caller. The creeper is someone you wouldn’t chat with otherwise, but because your friend is busy, you’re stuck.


The second type of wingman is the guy who’s attached at the hip to his friend, despite the obvious signs that it’s time for him to hit the road. The watcher’s greatest skills are lurking and making anyone in a five-mile vicinity uncomfortable. He seems unprepared to socialize without his friend, despite continued, obvious hints that he should hit the road. When a wingman doesn’t evacuate the premises, things get weird. He’s left watching his friend mack, which isn’t a comfortable situation for anyone involved, except maybe the watcher.

Our generation’s warped in many ways, and wingmen are one of them. Unfortunately, after years of drunken hook-ups, it’s left most of us awkward when it comes to dating in the grown-up world. Luckily, wingmen provide entertainment long after they’re gone, which is their greatest skill at the end of the day. So, wing-people of the world, try to be a little less creepy the next time you’re forced to make hours of awkward conversation for your friends. Who knows? Maybe it will improve your karma. Or you’ll end up having a double wedding, and all of your friends will be forced to find wingmen of their own.

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Margaret Abrams

Nothing Margaret writes should be taken seriously by anyone, including her parents, employers, or gentleman callers. She's currently coping with a quarterlife crisis.

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