Boston wingwomen to the rescue

What inspired you to start Hire a Boston Wingwoman?

I was already acting as a wingwoman for some of my friends—sort of propping them up as they sought out people they were interested in when we were out at night—and I noticed the positive effect it had on other people’s reception of them. My “Aha” moment came when Tyra Banks talked about it on her show, and I thought, hey, I can do that.

Why would someone want to use a wingwoman? Can’t they just go out with a friend, for example?

It can be hard to break the barrier in Boston. Having a wingwoman by your side just makes it easier to approach people. If you’re not a very social person, for example, you might not know where to go. We hold your hand, and help keep your eyes open to potential opportunities that you might miss otherwise. If it’s a situation where a man wants to approach a woman and she’s with a friend, we’ll chat up the friend so he can focus on his interaction with his prospective date. Also, sometimes women just want to go out with their girlfriends and don’t want to be approached by men. Our wingwomen are neutral, and can easily take these women’s defensive walls down by talking about something they can relate to. Once the conversation gets started, the barriers tend to fall, and the wingwoman can bring our [prospective male] client into the conversation.

Wouldn’t you say that relying upon another person to look better is just a sign of insecurity?

We have clients who are very confident—but just aren’t good at approaching other people. It’s something we assess through observation while we’re out with our clients, and if we notice areas where things can improve, we offer feedback and suggestions.

That said, I tell my clients that the best way to boost confidence while going out is through practice. Going out alone after work to a happy hour event is a great way to meet people and a chance to try things out without putting too much pressure on yourself. Hotel bars are great, too, because there are always people coming and going—and if you take a chance and it doesn’t work out? Odds are you won’t see him again.

Great ideas—I'm a huge advocate for going out alone. Do you have any tips on boosting confidence before it's time to go out?

First of all, you’ve got to take care of yourself. Make sure you’re working out and eating properly. If you’re newly back on the market and feeling blah, change it up. Try a new hairstyle, for example. Also, ladies: dress for your body type. It’s better to wear something flattering that fits and accentuates than something trendy. Guys want to see what you’re working with. And remember that if you’re out with your friends and you want to meet someone, you’ve got to make it a goal to go up to at least one or two guys while you’re out.

Where do people go wrong in approaching potential matches?

Among the biggest no-no's is interrupting a person's conversation at the wrong time. You've got to wait for the right time to approach, or else you'll start off on the wrong foot. Even if you've got the best opening line in the world, if I'm in the middle of an in-depth conversation with someone else and you barge in, that's the worst.

Describe your client base.

It’s mostly men who hire wingwomen, but we’ve had a recent surge in women who’ve utilized our services. We’ve worked with a lot of divorcees. As far as age, it ranges anywhere from early 20s to early 60s. Our younger clients are more apt to go out and meet as many people as they can, where our older clients want to know where to go and are choosier in their selections.

Where would you say are the best places to meet singles in Boston?

A big chunk of my job is to find out where the events are and to stay on top of it. I’d say museums, especially the MFA and ICA, and wine tastings are among my top recommendations. On a nice night, I’d recommend someone go to the Seaport District—there are tons of people there. If someone wants to get their money’s worth, in terms of meeting as many people as possible, I’d say for them to go to Boylston Street and bar hop, starting at one end and working their way to the end. Ultimately, you have to know what you want in another person before seeking it out.

How can someone tell that your service is successful?

I know it’s a success when I never hear from the client again (usually, it means they’ve met a person, hit it off and have gone on a few days). It’s rare for us to have a repeat client.

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