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Winging It: My Nights Out With a Professional Wingman and Wingwoman

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When it comes to dating, I’m not unlike a vampire: powerless until I’m invited in. I’m very comfortable on actual dates, when a woman has already agreed to spend time with me. But approaching a lady cold? It feels like an imposition. I can’t shake the feeling that the word “creep” is emblazoned on my forehead.

I tried to explain this to professional wingman Thomas Edwards when I met him outside of the Village Pourhouse in NYC on a Saturday night. “Here’s the thing,” I said. “I have trouble with this because I don’t ever want a woman to think that I’m hitting on her, even if I am.”

Thomas, a numbers guy, broke it down like this: The average woman out at a bar on any given night probably gets approached ten times from 10pm to 3am. Suppose she goes out twice a week. That’s 20 approaches every week, not including the times that she’s approached on the subway platform, in the park, in the coffee shop, etc. Add another 5 a week, conservatively. So, if she’s 26, she’s been going to bars for 5 years — that’s 6,500 times she’s been hit on before you come along.

“Huh. So, worst case scenario, I’m just another douchebag.”

Thomas laughed. “Exactly.”

And so began my first night out with a professional “wing.”

Most single folks are familiar with the concept of a wing

— it’s a friend who provides you with social validation when you’re out on the prowl. Your wing occupies the friends of women or men you’re interested in while you get to know them. What you may not know is that — like any art — “winging” has developed over the years. There are now skilled wingmen and wingwomen who have honed their craft and are able to charge for their services.

When I learned about this new profession, I couldn’t help but wonder if one gender or the other would be more naturally skilled at it. Would a man be better at helping me to meet women because he’s used to meeting women, or would a woman be better because she is one?

So, I enlisted professional wings Nafeesa Saboor (an employee of wingwoman and dating coach Courtney Crosslin) and Thomas (the numbers guy) to help me with an experiment. I planned to spend one night out with each of them in order to determine how much the gender of your wing affects your success rate in the field. Here’s how it all went down.

The Wingman

I imagine that I gulped like some kind of cartoon turtle as Thomas laid out the plan of attack: He would observe me in the field for the first 45 minutes or so, and then we would reconvene for observations and advice.

“What if I freeze?” I practically begged. “What if I can’t talk to anyone?”

Thomas clapped me on the shoulder and smiled. “I won’t let that happen,” he assured me. We approached the doorman.

“When you walk into the bar, know that people are going to notice you,” he instructed. “Take a deep breath and hold it. This naturally corrects your posture, sets your shoulders back and opens up your chest. It shows confidence.”

I was sure that everyone in the place would see right though it, but I took his advice, sucked in all of the air around me and walked into the joint like I was walking on to a yacht. The Pour House was a little more blazer-and-polo than I was used to, but the vibe was nice — cozier than you’d expect.

I approached the bar, with Thomas a few steps behind, and ordered a whisky. As luck would have it, there was a cute girl in a green off-the-shoulder top and a matching headband sitting next to me. Alone.

“You’ve got about thirty seconds to talk to the girl next to you, if you want to,” Thomas whispered in my ear.

“Right,” I replied, with an exaggerated nod.

And then I said nothing. Everything that I could think to open with sounded ridiculous. “Green, huh? You like green?” I imagined the girl’s blank, disappointed stare. She got up to join her friends.

Thomas saw another opportunity immediately. (He had apparently observed me enough to know that I was useless on my own.” “That girl just checked in on Foursquare. Talk to her about it.”

“Talk to her about what?” I thought. It was the lamest pickup line I could imagine. I knew I was going to embarrass myself, but I blurted it out before I could overthink it.

“Hey, I just noticed you checked in on Foursquare.”

“Oh my god, I love Foursquare!” she squealed. “Are you on it?”

Oh my god. It actually worked.

“Uh, yeah. I love it.”

It wasn’t long before Thomas and I were having a pretty natural, funny conversation with Foursquare girl and her friend. That’s not to say I felt comfortable, mind you. In fact, when I took out my phone to demonstrate my Foursquare expertise, my hands were visibly shaking.

The girls excused themselves to go sit down on a couch with their drinks and Thomas congratulated me. “That was a successful interaction. We could go talk to them if you want to.”

Now that I’d stopped convulsing, I did want to. We introduced ourselves and I learned that Emily, the girl I’d been talking to, was an intern at a major news network. She aspired to be either a war journalist or one of the ladies on The View. Thomas expertly kept her friend occupied as we talked and… I gradually lost interest. She was nice enough, but, well, young. In fact, most of the women at the Pour House were young. We soon learned why — it was apparently “Intern Night.” When the girls excused themselves to get a drink, Thomas and I decided that a change of venue was in order.

I remembered to take a deep breath and hold it as we entered Professor Thom’s, a slightly more grown-up, cavernous bar with a neighborhood feel, and let it out with an embarrassing, unintentional sigh. It didn’t matter, though. The joint was dead.

I sat down next to the only two women in the bar, and, though I wasn’t particularly interested in either of them, decided I could use the practice. The woman closest to me, a sunburnt blonde, was sipping beer from one of those fancy rounded Stella Artois glasses.

“Hey, is that actually Stella in there or did they just put it in a Stella glass?”

Thomas had taught me to start noticing details — anything is conversation worthy as long as it’s specific. It worked again.

“Yeah. But I know what you mean,” the woman said, “sometimes they just put whatever in there.”

The conversation flowed easily from there. It was a fun chat, but as before, I didn’t really have any desire to take it to the next level. Thomas and I politely, if abruptly, took our leave.

On the way to our third location Thomas reviewed my performance so far — two successful interactions with positive body language (apparently, they leaned in toward me) and genuine laughter. Supposing that I did want to take it to the next level, I wanted to know how.

“Physical contact,” Thomas enlightened me. A touch on the elbow when making a point, a hand on the shoulder or the knee when laughing would help me to gauge her interest and whether or not I should suggest exchanging numbers. By the time we got to the 13th Step, a rowdy crowded dance party was trying hard to happen in the skinny, dark venue.

I approached four groups of women and one guy, even. (Thomas said it’s good to talk everybody, because you never know who you’re going to meet. If you befriend a guy, he might invite you over to meet his female friends, one of whom could be, you know, your future wife. Every stranger represents an opportunity.)

My openers were as follows:

1. “What’s going on with that drunk girl on crutches over there? She’s going crazy!”
2. “Do you actually NEED those crutches, or are they just for show?”
3. “So, are you guys, like, huge Mariah Carey fans?”
4. “Does anyone actually like this song?”

I posed the fourth question to Josie, a cute Canadian, when NSync’s “Bye, Bye, Bye” came on and everyone started going wild.

“People in Toronto do!” she replied. I touched her elbow and she invited Thomas and me to another bar with her and her friends. When we got there, it turned out to be the same bar that we had begun our night at, and there was a line out the door.

Though Josie was friendly and cool, there was no real spark there and it was pushing 2am. I told her and her friends that it had been good hanging out, which it had, and Thomas and I took our leave to discuss what I had learned.

The Wingman Recap

1. Paying attention to details helps tremendously with conversation starters.
2. It doesn’t really matter what you open with. Just say something.
3. Talk to everyone. You never know where it will lead.
4. Practice, practice, practice.
5. Light physical contact will help you gauge their interest and connect.
6. Worst case scenario? You’re just another douche.

The Wingwoman

I met Nafeesa at 7:30 on a Thursday night in front of 1534 in Little Italy. She was exactly as she had described herself — afro, white shirt, lots of bracelets, really high heels.

It was clear from the get-go that she had a natural ability to make people feel comfortable and I guessed that it went a long way toward her choice of profession.

We made our way down the stairs to what turned out to be an exceptionally good spot – round leather booths, perfect lighting and a cool, knowledgeable mixologist who talked a good game. Nafeesa and I bonded over her appreciation of shoes (and my appreciation of her appreciation), and our ridiculously huge but delicious drinks. She told me that she ran a blog called Shoes and Booze (about her two favorite things) and she showed me photos of herself planking.

“Oh,” I thought to myself, “we’re just hanging out.”

It was a no-pressure approach. Nafeesa got friendly with the bartender and I followed suit. I barely even noticed that there was a cute photographer seated next to us, with 4 drinks in front of her. She was taking pictures for her blog. The photographer and I talked casually, off and on, as Nafeesa and I sipped our drinks. It didn’t feel like I was hitting on our new photographer friend at all. We were just a group of friendly people, hanging out and getting to know each other.

When Nafeesa and I decided to move on to a place that might be more crowded, it didn’t occur to me until after we left that I could probably have gotten the photographer’s number. That was something I was going to have to work on.

On our way to the next location, Nafeesa told me about her “Spider-Sense.” She claimed to have kind of inner compass that would tell her where we should end up. She would stop at an intersection, stick her finger in the air and move in the direction that she felt drawn toward. With another person, I may have deemed the whole thing to be new-agey bullshit. But on Nafeesa, it just seemed cool.

We ended up at Coffee Shop in Union Square.

“This place will be good because all kinds of people come here,” Nafeesa explained. With a variety of women around, she’d be able to get a better sense of what I was looking for.

Already, a key difference between wingwoman and wingmen was becoming apparent. Whereas Thomas had encouraged me to approach many women, Nafeesa was more interested in activating her intuition in order to find the right woman.

Nafeesa wasn’t kidding when she said “all kinds of people,” either — the place was like a really cool, really small airport. Coffee Shop was packed with sorority girls, financiers, older hippie types, and one woman that I was actually attracted to.

“The one with the hat?” Nafeesa almost rolled her eyes. “How did I know?”

Hat woman was gorgeous. A bit older than me, probably. Very put together, but chill. She seemed like a California transplant who had moved to the city to become a successful entrepeneur. Or something. She was certainly worth talking to.

“Write her a note.”

“What?” Now I was incredulous. “What do you mean ‘write her a note’?”

Write her a note. Make it corny, but not too corny. It worked on me once.”

If it had worked on Nafeesa, I was game. I asked the bartender for a dry napkin and composed the following masterpiece:

Nafeesa brought the note to Hat Woman’s table where she was sitting and having dinner with a friend. I watched, a knot in my stomach, and waited for Hat Woman to turn around. When she finally did, I hammed it up and flashed my Huey Lewis smile. The way that she buckled over laughing, I figured I wasn’t doing too badly.

Hat Woman was impressed, charmed, but non-committal. She created a “maybe” box and said that she’d join us when she’d finished eating if she we were still around.

Nafeesa and I had just gotten tired of waiting and began to walk toward the door when Hat Woman stood to hug her friend goodbye. I had written down my phone number, intending to hand it to her on my way out, but now I held on to it. I introduced myself, learned that her name was Veronica and she couldn’t stay long because she had to meet a friend to pick up keys for a dog-sitting gig. We chit-chatted, laughed at the absurdity of the whole thing and then she had to go. I slipped her my number and walked toward the door.

“Get her number,” Nafeesa whispered.

Oh yeah. I reeled back around. “Could I get your number actually?”

Veronica obliged. “I’m writing down my name, too, in case you forget,” she said.

“I won’t forget. It’s my favorite Elvis Costello song.”

She laughed. “No it isn’t,” she said, and walked down the street.

How did this happen? I had gotten a beautiful, successful woman’s phone number through the use of a note that a middle-schooler would have been embarrassed to write. Then, once we were talking, I was completely goofy. I understood right away why the interaction had been successful — I had been vetted.

All throughout our brief interaction, I noticed that Veronica was checking back in with Nafeesa, as if she was looking to her for assurance. The fact that this confident cool woman was vouching for me gave me some girl clout.

“She’s really good for you, you know,” Veronica had said.

With my confidence now up, and digits on a napkin in my pocket, we made our way to Down the Hatch (which was described by a woman I met there as “a little ‘How I Met Your Mother’”). One woman in particular caught Nafeesa’s eye — a tall blonde in a stylish orange dress.

“What about her?”

Orange Dress laughed a lot and she seemed to be the center of attention in her group. She reminded me of girls I had crushes on in high school, but never dated.

“Okay,” I nodded.

Nafeesa then coached me on how to look over in a way that would let Orange know I was interested, but not creep her out. I would look, then look away and Nafeesa would tell me if Orange was looking back at me. She was.

When I approached her she was involved in a heated game of foosball. I put my hand on a shoulder and said, “I got winner. So you better win.”

“On it,” she said, and returned to the game.

She didn’t win, but the reigning foosball champs let me and Orange take them on as a team anyway.

We ended up really got along. Laughing heartily. Crooning along to the jukebox. Losing the game. Badly.

I learned that Orange’s name was Alison and that she and her friend’s were going to another bar to dance. I was invited, but, Alison confessed, she had a boyfriend.

“I just like to have fun,” she said.

I laughed. “Well, in that case I’m not gonna come dancing.”

We shook hands and agreed that it would be cool to run into each other again some time and work on our foosball skills.

In the meantime, I had picked some vastly more important skills.

Wingwoman Recap

1. Going out with someone who makes you feel comfortable improves your game tenfold.
2. Approach women you’re actually interested in and who might be interested in you, too.
3. Being a little corny, but not too corny, gets you noticed — not in a bad way.
4. Having a woman with you gives you girl clout.
5. Look, but don’t be too obvious, and have someone else tell you if she looks back.
6. Being a little obvious is okay. You’re not actually expected to be that cool.

Wingman vs. Wingwoman: The Final Verdict

The differences between my Thomas and Nafeesa nights can be summed up in the same way that the differences between men and women are often described.

My wingman coached me to be confident and approach often. He was methodical, but acknowledged that bravery and instinct are a big part of the equation. He gave me the skills to do it on my own and encouraged me to practice.

My wingwoman focused making connections and harnessing intuition. The method was to hang out with her, be myself and seize the moment when it was right. Women who saw that I was with her felt more comfortable around me, and I didn’t have to work as hard. I felt comfortable, too.

What’s really interesting is that both experiences seemed equally successful. With Thomas, I had at least four successful interactions and got an invite to a second location. With Nafeesa, I had three successful interactions and got digits and an invite to a second location.

So, I still couldn’t say if men or women makes better wings, but what I can say is that having a wing who knows what they’re doing really makes a difference. With the right kind of support, a guy who’s shy about talking to strangers can go out and meet women. Multiple women, in fact. In one night. And, believe me, going out and meeting different kinds of people can really change your outlook about what’s out there for you.

I feel now, more than ever, that if the one for me doesn’t happen to be a friend of a friend, I’ll actually be able to approach her when I see her.

Think a professional wing could help you out too? Click here to get in touch with Nafeesa, or go here for 10% off a winging session with Thomas.

More like this:
5 Quick Tips for the Exasperated Wingman
Dating Tips from a Professional Wingman: Thomas Edwards
How to Be a Perfect Wingwoman for Other Women

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