Dating in Boston, although the city is a veritable hot-bed of overeducated single people and quirky restaurants, can be tough. reported in 2012 that “walking around the Common” is the most popular first date in Boston, although hanging around Davis Square in Somerville is a close second. For those of us who think walking around aimlessly with a cute person sounds terrifying, professional help is available!

Susan Baxter, founder and CEO of Hire a Boston WingWoman, says her lifelong interest in sociology led her to championing the art of breaking the ice.

“The interest I have in people and how they interact with others is what drove me to my Master’s degree and why I started this business.” Baxter and her staff of personable, friendly women (though one, named Margarita, looks suspiciously like a stock photo) are available for hire as Date Coaches, Image Consultants, and On-Site WingWomen, starting at $72/hour.

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An Image Consultation Before & After from the website


“We have more male than female clients,” says Baxter, “but the WingWomen work well with both. It’s interesting to see where our clients want to go, depending on their age. Usually clients in their twenties want to go to a club or lounge. Clients in their thirties like lounges or nice events, and forties and up like nice restaurants and more upscale events and fundraisers. We can make suggestions on where to go, or a client might want to go to a specific place he or she is used to. We’ll go to any venue with a client as long as it’s a public, safe space.” I did not ask Baxter for advice on date ideas, not because I wanted to avoid her reasonable fee, but because I’m still trying to get my boyfriend to take me to the New England Aquarium for their new Weird Lobsters of the World exhibit. I didn’t want to embarrass myself in front of a pro.

Baxter has cashed in impressively on a growing market in Boston: smart, funny, socially awkward singles in their twenties and thirties who are looking for love. Considering the rise of apps like Tinder (the company claims over 1 billion matches so far!), one might assume we’ve become so accustomed to quick gratification that our generation is getting rusty with our bar talk and in-person flirtation. Baxter seems to think dating in Boston is most effective if enacted with purpose, almost like a part-time job. Baxter says, “I always say to go to a bar during after-work hours by yourself. A lot of people need to unwind after a long day with a glass of wine or cocktail and are ready to vent about their day. Or, practice in a hotel bar because a lot of people are traveling and would love to know more about Boston (you can teach them a thing or two!) You are so much easier to talk to when you’re by yourself.”

Baxter and her staff are not opposed to online dating, however, and many of them even offer online dating profile consultations. “We’ll analyze your online profile and give you feedback on what to add/delete/change to get yourself noticed and sell yourself in the best capacity. Get advice on areas such as what tagline to use, which pictures will get you noticed the most, and what not to say in your profile.” (It is my assumption that “I hired someone to write this for me” is probably one of those no-no’s.)

The staff at Hire a Boston Wingwoman introduce their clients to potential mates at bars, guided by whatever criteria their client has laid out for them. Baxter says her staff, in order to be successful at hired events, must be ready to alter their appearance and demeanor based on their environment. “Our WingWoman will fit into any role,” she says, “depending on the atmosphere in which they’re working. For example, if a client wants to go to an upscale lounge, [the WingWoman] needs to play the part and wear high heels and something trendy. However, we also have clients who go to sports bars, and in that case, a WingWoman needs to wear something like a baseball hat and cutoff shorts.”

Baxter says the strangest gig she’s come across was a matter of intrigue. “One of our clients had a particularly interesting job for the WingWoman. He wanted to make his ex jealous. His ex taught a yoga class, and the client asked the WingWoman to go to the class with him and be friendly/fun/flirty with him. It totally worked. His ex was asking ‘who that girl was’ and the WingWoman was psyched because she got a free yoga class out of it!”


To contact Susan Baxter and Hire a Boston Wingwoman for their dating services, check out their website. And hey, ladies, if you’re a matchmaker who likes to wear cutoff shorts under her cocktail dress, you can always apply as a WingWoman yourself.