Winging It

In kindergarten, Lou Howe thought that Katie Kratovil was just fantastic, and he let her know—with frequent lollipops. One cold day in November, Katie approached Lou smiling sweetly. The moment had finally arrived. He puckered his lips expectantly—and then she poured a tub of glue on his innocent head.

Fifteen years later, Lou still hasn’t recovered. As his friend, I feel responsible for helping get this hunky senior back in the game.

If love is a battlefield, as eighties rocker Pat Benetar once noted, the struggle has only become more and more tactical in recent years, leaving Lou a little lost in the shuffle. But this year, single men have one more weapon in their pick-up arsenal, and it requires almost no work on their part: the wing woman.

The wing woman, like the more conventional wing man, takes one for the team, putting in all the work to meet a woman, without reaping any of the benefits.  Wing women are such a valuable weapon resource that Shane Forbes, a young New Yorker, has started wingwomen.com, a “ridiculously successful” service where a man can hire a smart, attractive woman to go out with and help introduce him to other women.

The role of the wing woman is simple: to initiate conversation with another woman, introduce the man, allow him to take over the conversation from there.

Is that really worth $50 an hour?

Forbes, who started his company after seeing the difference going out with female friends made, thinks so.

“If a guy talks to a girl at a bar, no matter what he says, the girl knows she is being hit on. This isn’t the case if the woman starts talking first. The girl isn’t defensive, worried that the guy has ulterior motives, which makes everyone more comfortable.”

I wanted to make everything more comfortable for Lou, so I decided to test the theory on him.

Friday night, Lou agreed to let me take him out. Our trip began at Noir...

10:30 p.m. Noir bar.

Walking to the bar, Lou and I finalize our strategy and are full of confidence as we pass by the bouncer at the typically dark and hip lounge at the Charles

Hotel. In planning our night out, however, neither of us took into account the

Red Sox/Yankees game — the bar is full of men, the lights are up, everyone is staring at the TV.

“This is weird,” remarks Lou.

As we order four tequila shots each to get our A-games on, a miracle happens: the bartender is really cute!  She smiles at Lou and gives him an extra shot.

Lou later points out that her flirting with him had nothing to do with having a

wing woman and was the obvious result of his irresistible charm. I point out that he’s wrong.

Encouraged by this first small victory, I start talking to a girl at the bar.

“Are you a Red Sox fan?” I ask. The voluptuous 30-something replies in the affirmative. We have a fabulous conversation. I introduce her to Lou. I think

I’ve mastered wing woman-dom. She goes to the ladies room.

Lou says, “veto.” We leave.

11:20 p.m. Redline bar.

I know lightning doesn’t strike twice, but I give it a shot. I order us four tequila shots, hoping another sexy bartender to bring them to us, but it’s a small bald man instead.

I spot a girl sitting by herself at the bar. “Are you an English major?” I geekily ask. She says that she is not, and turns back to the TV. I keep going, “because you really look like this girl who is in all my classes.”

Lou rolls his eyes; she shoots me a dirty look. “Ummm, do you go to Harvard?” I desperately ask. No, Tufts. Perfect, I think. “This is my friend, Lou. He has a really funny story about Tufts!”

Lou sweetly begins to tell the story of the crazy girl from Tufts who is currently sitting in his dorm after randomly facebook.com-ing his roommate—the girl gets up and walks away mid-story.

I feel rejected, but the show must go on.

I spot a girl dancing by herself. We hit the dance-floor. Lou scores her digits.

I decide my dancing was the deal-maker and pat myself on the back.

12:30 a.m. Brother Jimmy’s bar.

More tequila. Getting sloppy.

Before heading to Brother Jimmy’s, Lou and I had stopped by 7/11 and refined our approach.

A clerk behind the counter nodded in agreement when I suggested that maybe the reason wing women are effective is that women desire unavailable men; therefore, the new plan of attack involves pretending that Lou and I are dating.

We dance, even though no one else is, and look very much in love, I think, as we stumble around.

It works! As Lou goes to the bar, four girls approach me and start dancing to the song they requested. One is a very cute grad student at the school of education.

We have a great time, and when I introduce her to Lou, they instantly hit it off. I finally feel like I’ve been a good wing woman.

I leave them to talk for a little, and go say hello to some friends. Moments later Lou tackles me. “She just asked me if you are interested in men or women.”

We leave.

1:20 a.m.  Hong Kong.

En route to the Hong Kong, I take my wing-woman responsibilities seriously, inviting every attractive girl we see to the party Lou’s roommates are having later.

“Don’t worry,” I assure him, “you’ll have your pick of all the honeys.”

But we are both still sad as we approach the bar for our tequila, which at this point is a requirement. I stumble to a group of girls and try to think of something really interesting to say, something witty, something subtle. “You guys are awesome!” I slur. Luckily, at the Hong Kong after 1 a.m., everyone is in the same state.  “No, you’re awesome!,” the ringleader screeches back.

“No, you are.”

“You are soooo sweet.”

“No, you are soo sweet!”

Lou comes over. The ladies love him. They follow us out.

2:40 a.m.  Senior House.

Very, very unclear. Some sort of dance party.

A refrain of “who are all these random girls?” is heard throughout the party.

I go home, too tipsy to evaluate my performance for the night.

11 a.m.  Back at Senior House.

In the morning, I return to Lou’s room to ask him what he thought of his night, but sadly he is out already. I call him.

He kindly reports: “You were the worst wing woman ever.”

However, as I look around his bedroom, something catches my eye: a small pink cardigan sweater that definitely was not there the night before.

I skim over the outfits of the last night, trying to place it, but then I realize there are too many. I pimped my friend out well.