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."

What Makes the Perfect Wing Woman?

James tried again, at a sports bar a couple of weeks ago, ended with three or four numbers in hand.

"I don't think it's one of those things you do every week," he said. "I'd love it if one of the two or three people I'm seeing now worked out."

Baxter said she came up with the concept for her business after years of providing a similar service for free for male and female friends.

"I kind of saw that it worked. I feel like I'm pretty good at it," she said. "I just discovered that there are people that have this innate ability to go up to people, have more confidence than other people."

After turning 30 and realizing her career in medical equipment vending was not where she wanted to be, Baxter quit her job, did some research and launched Hire a Boston Wing Woman. She said she found there was a market where other businesses did well with the wing man or wing woman concept and wanted to tailor it to the Boston area.

Her slogan is "We're better at hitting on women than you are."

At first, she did the recruiting herself, hitting up bars and lounges and approaching attractive women who seemed to be outgoing. Now, she said, there's a waiting list of about 20 women who want to work as wing women.

"It's crazy," she said. "I have to turn people away at this point."

The perfect wing woman, she said, is easy to spot.

"She obviously has to be outgoing. Very confident," Baxter said. "She's attractive."

Baxter said she's not looking for women who are models, but that her wing women need to keep up with their appearance as well as the latest trends to come off as credible.

And there are rules for both wing woman and client.

The wing woman needs to be sensitive to what the client is looking for and keep within the boundaries of what makes him comfortable.

The clients, Baxter said, need to remember that the wing woman is not a date and Hire a Boston Wing Woman is not an escort service.

Wing Woman Dating 'Much Better Than Online'

James said he turned to Hire a Boston Wing Woman after hearing about it from a friend and then reading an article online not long after the company began taking clients.

After trying online dating and being disappointed with the results, he was ready to try something new.

Baxter said it's that idea of being able to meet someone in person without the fear of rejection that's appealing.

"If it works out fine, if not they can move on to the next woman he is interested," she said.

If a night out with the wing woman does result in a long-term relationship, she said, it's up to the client to decide if he ever wants to tell her how they really met. The wing woman, she said slyly, could simply be a friend that faded away.

She said her clients have run the gamut from "a player who wants to get extra numbers" to "the bookworm who doesn't get out of the house."

James insists he is neither, just someone who wanted to make dating in a busy city a little easier.

"I think it's a great way to go about it," he said. "It's much better than online."