Birds of a Feather

It's about time, I think, that the concept of wingman-- or wing person, what have you-- has entered the pop culture lexicon. For me, the word was first introduced in that 90's cult classic Swingers. Vince Vaughn’s character, T, asks one of his boyz, Sue, to play wingman while he goes and tries to pick up a girl he's been eyeing.

My understanding of the concept, and also my own practical experience, regards the term to mean a person who plays interference on the woman's friends while you engage the woman you're interested in meeting.

Not a tough concept to follow.

Unless you're in high school or are incredibly and shamefully awkward, under no circumstances should the wingman hook you up. The message will invariably be confused if a friend goes to do your dirty work. You always hook yourself up. The wingman's job is to, through witty conversation, urbane charm, and guileless humor, coax the girlfriends in the group who'll necessarily have a tendency kill your game. It's not an easy job because when girls go out in groups, the ‘decision by committee’ generally leads to the girl with strongest personality shutting down your chances—rather than you entirely making a fool of yourself.

This happens more than woman would like to admit: Groupthink decisions against your hook-up possibility. Therefore, the wingman just works the girlfriends: if the girlfriends are neutralized, your in a better position. Wingmen are always friends since trust in their ability is predicated on a wealth of personal history and shared experiences.

Although, now it seems that you can actually rent wing people for the night. This article on Yahoo News struck me as silly. Apparently, people are placing personal ads for wingman and women to accompany them out to bar in hopes that their chances of hookin' up with that special someone will be increased. Call me old school, but whatever happened to personal volition? Why not save the money and do it yourself. Better still—go out with friends who'll, naturally, do it for free. Sadly, this form of hook-up inanity isn't confined to the United States:

Jay O'Sullivan, a 28-year-old software developer in Montreal, can attest to the advantages of having a wingwoman along, especially with a group of guys.

"When you throw a woman into the mix, guys get competitive and try to be funnier," he says. "So the whole night just sort of takes off."

When O'Sullivan was planning a birthday party for a couple of co-workers last month, he posted a query on Craigslist, a popular online bulletin board, looking for wingwomen. "We just need some responsible girls to help keep the drinks topped up, the lines to the clubs short, and the cars idling. We are NICE GUYS who like to party hard," the ad read.

He had three responses and ended up choosing one of the women, who — for $100 Canadian and free drinks — helped the two birthday boys mix with the crowd.

"Ultimately, they didn't seal any deals, so to speak. But it was a good time," says O'Sullivan, who plans to use the wingwoman concept again sometime.

There is something profoundly pathetic about paying someone to hang out with you—especially if they don’t even help you ‘seal the deal’. What a waste. Why not just pay for a prostitute? At least that way your money is going to use.

Thus, the universal maxim with respect to the concept of a wing-person is that they be a friend—of some genuine stature. And lastly, of course, hook yourself up. If you're interested in that striking brunette standing at the bar, pensively fidgeting at her blouse, have the initiative to go introduce yourself. Make sure you have a couple of wingman to swoop in and entertain her friends.