“What’s your story?”

When approaching a stranger at a bar, that’s one of Thomas Edwards’s favorite opening lines. To Edwards, who’s a professional wingman, it’s more fun than saying “tell me about yourself” and is open-ended enough to get a conversation going.

But first: What’s his story? What exactly is a professional wingman?

He’s not a pickup artist. Edwards doesn’t teach his clients how to “neg,” or put people down while trying to pick them up. It’s far more positive than that. His goal, he says, is to teach his clients to be more comfortable in social settings — usually a bar — approaching strangers and becoming more approachable in the process.

“I help people develop the social skills necessary to create what will ultimately become a long-term relationship,” he tells me.

Now that online-dating is so ubiquitous, singles’ real-life social skills could use some help. Approaching someone in person feels more nerve-wracking when you don’t know who’s single, who’s looking and who’s in your age bracket. Presumably, when you’re meeting online, that information is upfront, even if it’s not always accurate. Online-dating is changing the bar scene, Edwards says. He goes to bars with clients and observes men, sitting at the bar swiping on Tinder while there are real, live prospects standing nearby.

When my colleagues Veronica Toney and Lavanya Ramanathan and I heard that Edwards has a “girlfriends strategy,” by which three friends help each other facilitate conversations, we invited him to come to Washington and teach us his ways. (Edwards is based in New York and works with clients all over the country; hiring him for a weekend, for example, will set you back $4,000, plus any travel involved.)

He taught us how to maintain open body language at a bar: by holding our drinks down low, away from our chest; and fanning out in a row rather than clustering in a tight circle. Edwards talked to us about how touching a person’s arm or gently edging into their personal space can make a conversation feel more flirtatious. That last piece of advice might sound like common sense, but the body-language stuff required more conscious action on our part.

We also took on different roles throughout the night — I played the “facilitator,” popping into groups and starting conversations, then finding a common interest that I could use to bring in Veronica or Lavanya. And we absorbed his tricks for getting out of boring or dead-end conversations — saying “it was nice to meet you” or, if needed, coming by to hand one another a drink to help someone out of a conversation. With three of us involved, it meant that I could exit a conversation once Veronica or Lavanya felt comfortable. It’s easier to maneuver in and out of conversations with a group of three than with two, I learned.

I’ve never thought of myself as a particularly good wingwoman. Maybe that’s because I’m pretty direct; subtlety is not my strong suit. So when Thomas showed up, I wanted to learn how to better facilitate connections among my friends, focusing more on getting people into and out of conversations than trying to speak for them.

“When you meet someone in a bar,” Edwards says, “I like to think of it almost as a micro-date. You’re just meeting someone and you’re trying to get a gauge of what their chemistry is like.”

So how did our micro-dates go that night? I got a lot of joy out of seeing Veronica and Lavanya get more comfortable in conversations with strangers. By the end of the night, we’d talked to about a dozen of the men at Black Jack on Washington’s busy 14th Street corridor. By actively seeking out new conversations, the bar began to feel more like a party than a room full of strangers. I ended up exchanging phone numbers with one man I’d been talking to — and with whom I’d leaned in for a kiss as the conversation got cozier — but I chose not to see him again.

I’ll let my fellow wingwomen speak for themselves. Veronica’s challenge was to unblur the line between friendly and flirty:

Talking to strangers has never been a problem for me. But when it comes to picking up guys at bars, it’s just not something I do. For one thing, I’m not a big toucher (I even wrote a story about it), so you won’t find me arm-grazing or playing footsie under tables. I believe that leads guys to mistake my flirting as just being friendly — it gives them an opening to ask whether my friends are single.

While I still had no problems approaching people, I did have a hard time carrying on a conversation. It’s really hard to talk, ask questions, respond in a clever way, remember not to hold my drink at chest level, decide when or if I should move in closer, and remember to smile. At the end of the night, I had talked to a few nice and attractive men, but I was exhausted.

Since the night out with my wingpeople, I’ve found myself striking up more conversations to test Edwards’s theory that practice makes these tips less daunting. The results haven’t been any different, but it has been nice to put in more effort, even though I’m sure I’ll be back to my jaded self in a few weeks.

Lavanya’s challenge for the evening was to get out of interview-mode:

Being a reporter means I’m pathologically unafraid to approach people, in grocery stores, on the dance floors of clubs, in the crowd waiting for the pope. But that hasn’t cured what has been a lifelong (maybe cultural) aversion to talking to dudes I’m interested in. When she heard about this little experiment, my own editor jokingly referred to me as “a push-away artist.” I have NO game, and apparently, everybody knows it.

So, more than Lisa and Veronica, I probably needed Edwards’s coaching. (My mom would heartily agree that I need something.) And Edwards’s advice, particularly his encouragement to seize on a characteristic about a person and engage them, to not take it all so seriously, worked in practice. Every time my wingwomen approached someone, conversation ensued, often with nice, funny guys. And yet. Maybe it was the venue – a bar full of 20-somethings – or just me, but unlike my wingwomen, once we were out, I was unwilling to put myself out there, even if it was just for practice. I couldn’t wait for the night to be over.

I’d love to be as unafraid as Thomas and my wingwomen, as unfazed by dating. But I also realized something about myself: I won’t ever see men as conquests or flirting as an ego boost. My shyness hasn’t left me pining or lonely. I still have no game, but for now, it works for me.

To hear more about our night out with Edwards, listen to the latest episode of the Solo-ish podcast below, or download it on iTunes.