On a Wingman and a Prayer: Singles Bow to Cupids-for-Hire

As romantics grow weary of the digital dating game, so-called wingman and wingwoman services are taking them back in time. Such outfits, which popped up in cities like Boston and New York as long as eight years ago, are promoting the old-fashioned tête-à-tête. They’re gaining traction at a time when Internet dating sites are attracting fewer visitors. Susan Baxter, founder of “Hire a Boston Wingwoman,” says she launched her business specifically because her friends were fatigued by online dating. She sensed a good niche. “You go to meet [the person] and realize their picture was taken 10 years ago and that they are not who you thought,” says Ms. Baxter, 32 years old. Paired with a confident wingwoman, her customers “can see prospective partners right away, and know right then and there if there is chemistry.”

Ms. Baxter, whose fees start at $130, insists that clients who go out with a pro have better odds of success than those who troll with an untrained male buddy. Often, the friend “says stupid stuff, like ‘my friend thinks you’re hot,'” she says. The service’s slogan: “We’re better at hitting on women than you are.” While online dating sites have changed the dance of romance, academic researchers have been skeptical about sites’ purported “success” (code word for marriage) rates. And the Federal Bureau of Investigation, which handles Internet crimes, says it receives thousands of complaints annually from people who get scammed by shady suitors. In an ongoing lawsuit filed in federal court in Dallas a year ago, several Match.com customers sued the company, saying that many of its profiles are phony or are linked to inactive members. A spokeswoman for Match.com calls the lawsuit “frivolous.” The wingman has been on the dating scene since the days of Shakespeare, when Romeo’s closest pal Mercutio helps him to forget a girlfriend by taking him to a masked ball at Lord Capulet’s estate to meet other women (in the end, that didn’t go well). More recently, the wingman has been celebrated in movies like “Hitch,” a 2005 comedy starring Will Smith as a professional Cupid. Most services say they tend to focus on male clients, the theory being that men need more help since women often go out in groups, making it harder for a lone guy to break in. But the wings-for-hire say they do sometimes fly with female clients, too. Josh Mitchell, 27, started his Indianapolis wingwoman service, “Miss Pivot,” last year after attending an event for young entrepreneurs. Romance aside, there was something else that convinced him he had a winning concept. No one, he says, seems to know how to have a face-to-face conversation anymore. “A lot of social skills you used to pick up watching your parents, but now everyone is busy watching stuff online or playing videogames online,” he says. Mr. Mitchell now runs Miss Pivot with a team of five friends, including a “head coach,” plus eight freelance “pivots” for hire at $45 to $65 an hour.

Not everyone is cut out for the matchmaking work. “We don’t want someone with a really annoying voice,” says Mr. Mitchell. Another no-no: overly emotional types. “They tend to think love is very magical while we think there is a science behind it,” he says. For the dates, the pivots generally stay away from nightclubs, and go to bookstores, coffee shops or pubs where the tables are high. “Sitting on stools brings everyone up to the same level,” says Mr. Mitchell.

If you cannot approach a very attractive woman without help simply to strike up a charming conversation and eventually secure a date, you are a pathetic creature. And ladies, a nice smile and a simple hello will do. Trust me, if he is at all interested, he will take it from there. Enough done on your part. There, I just saved you hundreds of dollars! You can thank me later. 🙂

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