Why Wing It? Hire a Pro!

We’ve all had at least one well-meaning friend who fancies themselves a Cupid. Sometimes these meddling matchmakers operate through generalities (“You both watch ‘Game of Thrones’! It’s a sign from the cosmos!”). Other times, your romantic ambassador may truly have a preternatural eye for chemistry. Then there’s the valuable friend who is simply brave and outgoing: your go-to wingman, ready to talk you up to interesting strangers. There’s never been a gender lock on this sort of behavior. Men wing for friends, female and male alike. So do women.

Whether it’s because we’re living in a post-pickup artist world, no longer whole-swallowing the methods of men in silly hats as the ultimate seduction techniques, or because we’re becoming more woke to the ways women can feel pressured when dating, there does seem to be a general trend. We’re hearing less about the Hitches of the world — and enterprising women have turned the demand for the female perspective into actual businesses.

If you don’t trust your female friend to do the job, you can hire a professional wingwoman. They exist. Some, like New York’s Erin Davis, profiled both in the New York Post and Narratively, call themselves by other terms — Davis uses “strategic introducer and ice breaker” on her website, although she doesn’t eschew the term wingwoman. Davis charges $100 an hour. Then there’s the Boston-based company, Hire a WingWoman. Formed in 2010, prices for hiring a woman to wing for you in bars and lounges around town run at $96/hour, with a two-hour minimum. It’s an uptick from 2014, when the service charged $72/hour, according to a write-up in Marie Claire.

Others do it for the love of the game. Brittany Hunt of Warwick runs Top Wingwoman. Calling it more of a side hustle — and on a temporary hiatus (expecting moms generally avoid the late

night singles scene) — Hunt has been winging for friends formally and informally for 10 years.

“If you can make a joke, that’s the best way to approach someone,” Hunt says. “I don’t mean a corny pick-up line, but if you can make a joke, that’s the best way to set people at ease with introductions.”

Once a friend identifies a person they’re interested in meeting, Hunt finds a “non-aggressive” way to approach by assessing the environment. “You have to observe what they’re doing,” she explains. “If there’s a game on and they’re watching the game, you can get a sense of what they’re interested in.”

If some of Hunt’s tactics, like making eye contact, seem obvious, consider the dating culture. Tinder boasts that they set up 1.5 million dates per week. It doesn’t feel like much of a stretch to wonder if the amount of time we spend staring at our screens and swiping hasn’t caused erosion to the IRL fundamental motor skills.

Yet, consider what happened just this month when technology tried to step on wingwoman turf. Alexa, through a partnership with Match.com, recently added a new skill offering people advice, designed to boost their confidence before dating. The skill answered questions like, “What if I want more than one drink?” with answers like, “Allow yourself two cocktails if they’re cute. Have six if they’re not.” Unsurprisingly, the app was pulled from Alexa’s skills after less than one week. (Likely inspired by Alexa’s answer to “What is consent?” – “LOL!” – and the subsequent public reaction.)

While friends and professionals do the job better than disembodied robots, a wingwoman or wingman can only take you so far. Tyler Loiselle, also of Warwick, has served as a wingman both paid by clients and unpaid for friends. He and Hunt were approached to be the wingman and wingwoman for a dating app, although a final deal was never reached.

Loiselle describes a night at BLU, winging for his friend, (we’ll call him “Connor”). “A group of four beautiful, like, out of everyone’s league women were there. I was with a group and we worked our way in because all the guys who were approaching them were solo. But we had a group that matched theirs in numbers. There was a girl Connor liked, and I spoke with her for 10 or 15 minutes. Eventually I got into more specifics about Connor, his situation, he’s a good guy, someone you always want to have in your phone. You need to let people know that the dude you’re winging for is a good friend first.

“By the end of the night, he’d been dancing with her for a long time,” Loiselle says. “They paired off. There was this opportune moment for him to get her number and he just flat out didn’t ask. Never fucking made the move and I’m still upset about it to this day. The situation and scenario were perfect for Connor. There was no competition, and he still didn’t follow it through. If you’re playing tee-ball, the wingman’s the tee. You still gotta hit the ball.”