Wing Woman of Your Dreams: Dating Serivce Takes Sting out of First Introductions

Nov. 24, 2010— -- Too nervous to ask out that pretty girl sipping a martini at the bar? No sweat -- your wing woman's got it covered.

After generations of men employing the much touted "wing man" to help score dates, Bostonians are beginning to turn to the female counterpart to infiltrate the often intimidating inner circle of girls night out.

So-called "wing women" are the sole employees of 31-year-old entrepreneur Susan Baxter, who launched her dating service, Hire a Boston Wing Woman, in September and already averages between 15 and 20 clients at any given time.

"When I started this, and when I had the concept, I thought this would all be working men in their 30s or maybe 40s," Baxter said. "Come to find out I have a lot of guys in their mid-20s too, I would say, mid-30s and there's a couple of stragglers in their 40s."

The men pay Baxter to provide them with a professional wing woman who -- for $65 an hour, minimum of two hours -- will accompany them to a bar or lounge and sidle up to attractive women with the ultimate goal of making that first introduction before fading into the background.

"It's intimidating to go up to hot women or hot guys," Baxter said. "I thought Boston could use it because it's a really conservative city."

Baxter, who lives in Boston and has a degree in applied sociology, said her dozen or so employees begin the evening with a brief conversation with the client to get a feel for what type of women he's interested in. They also discuss their own back story -- are they friends? Cousins? Co-workers?

Once the client picks out a woman he'd like to meet, the wing woman will then find a way to strike up a conversation with her and her friends, maybe complimenting an outfit or overhearing part of the discussion that she could then use to show how much the woman and the client have in common.

So far, Baxter's wing women have gotten good results. Testimonials on her website report that the clients have come away from the evening with a pocketful of numbers.

For James, a 36-year-old Bostonian who did not want his last name used, it was a way not just to meet women but to get a better handle on the atmosphere of the city, which he still struggled with three years after moving from Chicago.

"It's a great place, but I found that most of the people I was meeting, or when I went out, they had all lived here for a long time. They had their own friends," he said.

So James, who works in investment banking, hired a wing woman -- twice.

"It was a little weird at first," he said, quickly adding, "she was very good."

"The first night I probably got three numbers," James said. "I've been out a couple of times with a couple of them."