Memoir: Winging It

Top GunWhen I first read the ad, I was convinced that it was an attempt to recruit me into a prostitution ring. The wording was: Are you beautiful? Upbeat? Outgoing? Do you like to help your male friends meet women? Come work as a wingwoman for our dating coach service. $35/hr.

However, because I had just moved to New York City and could no longer stomach a diet solely of ramen noodles, I sent in a very long response stating that while I was indeed, upbeat, I was not willing to exchange sex for money. I think I may have also said that I was not into any sort of foot fetish or dominatrix thing either, if that was what they had in mind. I received a note back from a very understanding dating coach saying that was great, because he wasn’t into any of that either.

He explained that wingwoman-ing basically consists of going out to bars with a typically nice but shy and nervous man and striking up conversations with other women. To be fair, it is a lot easier for a woman to go up to another girl and say, “Hey, I like your shoes, where’d you get them?” than it is for a man. After talking for a bit, I introduce her to my friend (I always make sure to mention that I have a boyfriend, and this is my old friend from college or someplace similar, so the girl knows I’m not dating him) and then I cross my fingers and hope that the two of them hit it off.

A year and a half after I first fluttered my wings, my food budget is much improved, but I’ve never given up wingwoman-ing. Why? Because 90 percent of the time, it’s a really fun gig.

Of course, some cynics assume that all the men are creeps and that they’re only looking to get laid. I’ve never found that to be the case. Most of them are ludicrously sweet people. And they’re definitely not looking to just get laid (though many of them seem as though they have not been laid in a very long time, and if they ended up going home from the bar with a girl? Well, I’d be pretty happy for them). Still, there are probably cheaper and easier ways to find a one-night stand.

They really do want relationships.  It’s just that – whether they’ve just been divorced, or are in their early 20s and don’t feel confident with women, or are in their 30s and still live with mother – they’re not very good at initiating conversations to make women want to know them. I’ve seen men describe their ideal honeymoon spots to women they have just met (he literally asked her if she preferred Venice or Rome), men misuse pick up lines (one asked a woman if she was an ax murderer, then forgot the second half of the pick-up line – I still don’t know what that part is – and left the woman looking very confused and scared), to men who have desperately tried to get all their flaws out of the way up front (don’t explain to her that you have six toes and drool in your sleep in that first conversation).

And many of them are painfully shy. Like the really good looking fellow who began our introductory conversation by explaining that he had social anxiety disorder and that, at age 26 had never had a real girlfriend. “Maybe we can start changing that tonight!” I declared brightly. “No,” he replied, “I’m really, really nervous about this. Really nervous.” I scaled back. “Okay,” I said, “well, we can just sit and talk for a while. About your interests. And maybe the sort of girl that you’re usually attracted to.” “I’m really nervous,” he replied. Then he leaned over, and vomited all over my new shoes. That is the 10% of the time that it’s not such a fun gig. But honestly, those are the men that you root for the most.

And when I hear back that they are actually dating someone they met when we went out (it doesn’t happen all the time, but it does happen)? Well, it sets my little heart a-flutter.

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