Don’t Call It an Escort

Can female friends turn you into a pickup artist? Jason Schwartz hires a wingwoman to find out.

Illustration by Kirsten Ulve

Illustration by Kirsten Ulve

Picking up women at a bar isn’t easy. Neither is ice road trucking or being from New Jersey. If they were, there wouldn’t be reality shows about them. That’s presumably the thinking behind Hire a Boston WingWoman, a service that, for $65 per hour (two-hour minimum), arms you with a female copilot. She’s trained to strike up conversations with ladies and then subtly bring you in. Ideally, this results in the acquisition of, ahem, mad digits.

As a (slightly twisted) nod to Valentine’s Day, my editor directed me to give the service a spin and report back. After paying in advance, I met my assigned WW at the Cambridge hangout Cuchi Cuchi. In her late twenties, she wore jeans, a blazer, and bright-red lipstick. She was impressively outgoing. Sadly, that wasn’t nearly enough to overcome our awkwardness; we spent the first half-hour trying to get over the fact that I had contracted her to be there. (It helped that I drank a lot.)

When we finally got down to business, though, it ended up being sort of fun to have someone be the icebreaker for me. Unfortunately, girls aren’t stupid: When my WW tried to pivot me into conversations, it was pretty transparent. Thankfully, most of my targets were too polite to groan out loud. There was one promising moment when my WW volunteered my services to snap a photo of some ladies. Alas, through the lens of the camera, they looked all of 18. If that. (Side note: Cuchi Cuchi originally seemed perfect, since it’s filled with girls’-night-out groups. But my research indicates they’re on a girls’ night out because they’d rather not be bothered by boys.)

Next, we made our way to the Enormous Room, which is quite loud, making it a tough place to meet people. Especially if, like me, your dancing makes Elaine Benes seem graceful. After a few more failed attempts, my WW took off for the night.

All in all, I’ll admit she did jump-start some fun exchanges for me, but no phone numbers resulted. In fairness to the company, it’s conceivable I had something to do with that. In fairness to the rest of you, I’ll advise this: If you insist on spending $130 to chat up women at a bar, just open a tab and dole out drinks. Everyone will feel much less weird about it, and that’s even before they’ve had a sip.