Winging it

In the age of online dating, much digital ink has been spilled on the subject of how to successfully meet people face-to-face, and the bar is a go-to venue for dusting off your atrophied social instincts. I say that without irony, as I personally consider approaching a total stranger to be daunting when I’m not sure how my efforts will be received.

Reading articles like the Washington Post’s account of a “professional wingman” (think more “etiquette coach” than “sleazy pickup artist”) can seem like a laundry list of dos and don’ts to be remembered simultaneously while flirting—things like maintaining open body language by holding your drink low and away from your chest and asking the right questions to establish common interests. But some of the theories also made sense to me.

I decided it couldn’t hurt to practice being more approachable, so with reference material in hand, I enlisted my brother, Sean, and two friends, Steven Carlson and Krista Anderson, to meet me at the bar to come up with a game plan. It immediately became a slightly awkward conversation: we’d never engineered a plan to meet people at bars before, and now we were trying to strategize something that’s typically an organic experience.

Since we are all within the same age range, I assumed our experiences at the bar would be fairly similar. Still, with Krista being the only female of our group and my brother having spent the past few years attending college in Southern California, it became obvious we didn’t have a consensus on what works best when approaching—or being approached—by someone new.

We started by discussing the seemingly obvious interaction of buying someone a drink. Pop culture would have us believe that this is the expected way to introduce yourself to someone waiting at the bar, but the real-world circumstances that determine whether or not someone will appreciate such a gesture range drastically.

“I wouldn’t buy a drink for a girl unless we’d already been talking for at least a little bit of time,” said Sean.

In his experience, starting an interaction that’s dependent on buying a drink is already problematic. Instead, he felt like it was more appropriate to offer a drink as a way to extend a conversation he might have already been having. That way, at least he knew there was interest beyond the just the drink. Also, it avoids the implication of putting someone “on the clock”—or assuming you’ve bought their time.

That assumption, Krista agreed, was a definite way to cheapen what could otherwise be a nice gesture. Buying a drink, she said, shouldn’t obligate anyone into a conversation—let alone anything more.

“I will definitely say I’m hesitant to accept a drink because a guy might expect something in return,” she said. “I think if you’re genuinely just trying to talk somebody and you don’t have this intention like, ’I’m going to take you home tonight,’ then it’s normal—it’s a more natural conversation.”

By this point, we all agreed that buying a drink wasn’t as necessary as being genuine with your interest in someone in the first place, and that no one wants to feel obligated in a social setting. The assumptions that crop up when drinks are bought, we also agreed, must be pretty universal.

But in reading an article called “How to Flirt with a Girl at a Bar, According to Girls,” we came across a suggestion that none of us had ever encountered before: If you buy a drink for her, you should also buy one for all of her friends.

We thought this was outrageous, as none of us guys had ever felt required to do that—nor could we afford it—and Krista had certainly never expected anyone do that. In seeking an outside opinion, I introduced myself to Holly O’Connor and Kat Krakowski, who were at the bar celebrating Kat’s birthday.

“I don’t feel like a lot of guys just go up to a girl and want to buy them a drink these days—that has changed a lot,” Holly said. “So for them to buy your entire group a drink, that’s crazy to me. I’ve never had that happen.”

I was relieved to hear that Kat also agreed and that I wouldn’t have to drastically increase my budget for future nights out. Once again, they agreed that accepting a drink doesn’t necessarily mean they’re more inclined to speak to anyone, and that guys should instead pay attention to any cues that indicate interest in the first place.

“I think your body language changes, you know,” Kat said. “You try a little harder with how you look. You laugh more. I think that girls definitely play with their hair more. They kind of glance over there. It’s definitely the traditional flirty thing.”

I thanked Holly and wished Kat a happy birthday and returned to my table, vindicated that we weren’t totally off on our understanding of dating culture, and with renewed skepticism of any coordinated dating plans. It also struck me that I had basically just done what I set out to do: initiate a conversation with women at the bar.

By approaching with genuine interest and with no other intentions except to ask their opinion, we had a natural conversation where nobody felt pressured or otherwise had their night disrupted. When I introduced myself as a journalist who wanted to talk about dating, it even took them a minute to realize I wasn’t just using the world’s worst pickup line.

I was beginning to suspect that over-preparing for a first encounter might not be the best way to meet people—but I felt like I needed at least one more male opinion on what, if anything, makes for a successful dating strategy.

I ran into my friend Nate Emme later in the night, and he introduced me to the larger group of friends he was out with. I asked them what they felt was the most important factor for meeting women.

“It’s confidence above everything,” said Corey Allan. “Whether it’s interpreted obviously or on a subconscious level, I don’t think any girl at a bar is going to enjoy you seeming like you lack confidence.”

The line between confident and obnoxious, however, is easily crossed—especially when you’ve been drinking—and resorting to backwards male stereotypes like being the “alpha” can come off as both offensive and desperate.

“An over-masculine presence is definitely a turn off most of the time,” said Matt Egan. “If you’re trying to push your masculinity on women, they usually don’t like that.”

“If you start off super desperate, you’re done,” agreed Nate.

Ultimately, the consensus was that being respectful and honest when asking for someone’s attention is important—especially if sex is your end goal. It’s important for men to remember, but equally applicable to everyone—and it seems to be a better plan than any other tips you’ll read about online.

“Above all, it’s just realizing that you’re a human being, and they’re a human being,” said Julian Emme. “Don’t put on a weird front to get with somebody because, if it works, it’s going to screw you over. You’re going to feel really bad in the end.”