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Do you have what it takes to be a professional wing woman?

There’s a new breed of cupid in town: the professional wing woman. Instead of a bow and arrow, she uses charm, a smile and sparkling conversation to hook her clients up. Intrigued? SheKnows chatted to two professional wing women to learn more about this fascinating new dating trend.

The logic is simple: Use women to help pick up women.

A man in the presence of fun, non-threatening female friends is far more disarming than the guy leering over from the side of a bar, surrounded by a posse of male companions. Ingenious! In fact, it’s so brilliant that it has sparked a nationwide revolution — professional wing women are taking Canada by storm.

But how does it work? What does it take to be a professional wing woman? How can you spot one at a bar? And do the clients fess up to their partners about their use of a professional matchmaker once their fairy tale takes off? We chatted to a couple of professional wing women to find out.

What is a wing woman?

Not all men are blessed with attractive, fun and — most important — platonic female friends they can take to bars as a way to meet potential matches. So in essence, a wing woman is a stand-in for exactly that.

“A wing woman is a professional ‘friend’ that you hire to go out with you in a social setting to help target the opposite sex, opening you up to the possibility of meeting a potential partner,” explains Shanny in the City matchmaker, dating and relationship expert and professional wing woman, Shannon Tebb. “[She] selects the right venue and scopes out the environment for potential targets. She finds a way to initiate conversation, bring the client in and then entertain any friends to keep them away so the client can chat with the target.”

According to the founder of Toronto Wingwoman, Candice A, the role also involves a bit of tutelage. Aside from matching people up, she says a good wing woman also helps her client to become comfortable with himself so that he uses his own personality — rather than a gimmick — to make a real love connection.

What does it take to be a wing woman?

Not surprisingly, facilitating a meeting between two strangers takes a certain level of suaveness as well as a set of rather specific skills.

A wing woman not only has to be professional, polished, well dressed, creative, outgoing and disarming as a conversationalist, says Shannon, but she must also know how to include her client in a conversation that she’s started.

“She must be caring and passionate to help people,” agrees Candice. “She must be understanding and intuitive, learning how to read more of what is not said rather than what is said. She also needs to be resourceful to help her clients find the best spots in the city where they can meet potential partners.”

“She can read a room within seconds and scope out the single versus the taken women,” adds Shannon.

Who uses a wing woman?

A friend-for-hire can lead to the misconception that the men seeking her out must be unattractive introverts who live in padded rooms and collect toenail clippings.

Not so.

For the most part, the men who use the service are busy professionals who simply don’t have the time, means or confidence to meet the sort of partners that strike their interest. Shy? Yes. But creepy? No.

“Usually they’ve always been shy, but since being out of a formal school environment, [they find it] harder to meet people. They are looking to meet long-term partners and want to find out how to select proper people,” explains Candice.

Most wing woman services involve a vetting process to screen out any men who might want to take advantage, which means only serious clients are taken on.

Not as easy as it sounds

Sound easy? Meet a nice guy, take him to a cool place, introduce him to a nice girl, and watch the sparks fly? Well, there are a couple of little obstacles every wing woman must tackle.

The first thing, of course, is understanding your client and what he wants so you know what you’re looking for in terms of a potential match.

“You may think that [a woman has] the right look for your client, when he may not be attracted to her at all,” says Shannon.

Another obstacle might be the client himself — if he’s nervous, not accustomed to flirtatious situations or just socially awkward. Every wing woman needs to be prepared to react if a client freezes up and doesn’t join the conversation.

“Having the guy follow you around in fear rather than make an effort to connect can also give off a negative vulnerable vibe,” Shannon adds. “The client must be ready and prepared to stand next to me with confidence rather than behind me with fear.”

“A funny challenge is when they think I am a date or girlfriend. So it’s really important that I maintain the ‘buddy’ card by not standing too close,” she continues. “The strangest request I got was to attend a wedding with a client as his personal wing woman. This was not going to be an environment to scope out singles, as the majority of guests were there on dates, so I politely declined.”

And, of course, not all clients were created equal. Because of this, Candice says that being able to change your approach and remain positive even when things go awry is necessary.

“Not every solution works for everyone, and you need to be the cheerleader for your client, keeping their spirits up,” she says. “You also need to be creative to find out why a certain approach isn’t working and in essence be an ‘attraction detective’ to find out what you can do to modify the situation to put the odds in your client’s favour.”

Single yourself? Take the “Am I good wife material?” quiz >>

The rewards

Naturally the job comes with a few perks — happy endings being at the top of the list.

“The most rewarding part of the job is seeing a client’s confidence reach a higher level,” says Shannon. “Seeing him connect with a female and make a lasting impression.”

Her favourite success story is of an introduction she made that resulted in a marriage.

“I had been hired as a wing woman to attend a wine-tasting event. It was packed with people in good spirits, with lots of familiar faces. I played the ‘buddy’ card and introduced him to various women that day, one of which he actually dated and married after two years!”

Likewise, Candice finds love successes to be the highlight.

“The best part is when your clients write back and either inform you they met the partner of their dreams or simply when they write back to say they have found a new sense of confidence now that not only has helped them in their love lives but also in their professional lives.”

Breaking the news

To tell or not to tell? That is the question. Should — and do — clients reveal to their partners that the cool co-worker or friend through whom they met was actually a professional?

It seems the jury is still out on this one. Candice encourages her clients to tell their partners.

“This has never posed a problem, as we only work with clients who are sincere about finding romantic connections and use our services as a means to get over being shy,” she says.

Conversely, Shannon says her clients often keep the use of the service a secret.

“My clients often don’t discuss the notion of hiring a wing woman, as they would rather keep this confidential. I am introduced as a friend or new co-worker if we bump into someone we know.”

Although, she adds, sometimes the odd client brags to his friends about what he’s up to.

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