Dating Clinic: How (Not) to Talk to Strangers

Couple standing outside a tropical restaurantI recently attended a singles event in Manhattan sponsored by an online dating site. The bar had lots of atmosphere—but very little A/C, so it was social, but sweaty. And while the crowd was very squarely adult (average age probably about 35), you would have thought it was a high school mixer. Women sat along one wall, or chatted in small groups, while the men hunkered around, some looking slightly uncomfortable, others leering in wait like lone wolfs.

This never gets easier. But still, the people in this room had made the Herculean effort to get there—RSVP’d days in advance, got dressed, took the train or a cab across town. Got there. Walked in. They were about as committed to being here as you could be. And then, it seems, stopped short by their own stories, assumptions, and judgments.

The “Everyone Here Sucks” Excuse

I spoke with a clatch of women sitting along the window bench (p.s., forming a female firing squad is not a great way to meet men), who were quick to bring me into their ranks. “Is this your first time? Here, sit down with us!” When I asked what they thought, the ringleader said she’d already done a lap, and in one facial twitch, dismissed the crowd of men outright. Why? “Eh,” she said. Too old, not goodlooking enough, not my type. (None of them?) In one lap she’d figured this out.

“How do you know that?” I asked. There were some silver foxes in the mix for sure, but on the whole it wasn’t a bad looking crowd. It was essentially shooting fish in a barrel—for men and women. The woman who claimed the men were too old for her also told me she was 38. “I hate to break it to you,” I said, “but these men are in your—our—range. They’re not too old.”

“Well, we don’t see anyone worth talking to, so in a bit, we’re thinking of going to a bar down the street.”

A bar down the street? They’d made every effort to be here now, where available men were guaranteed. This is another easy strategy for avoiding talking to people here and now–that everyone you want is somewhere else. Another convenient piece of fiction to sell yourself. What on earth would make this woman think that the men of their dreams were two doors down? I wished them luck and moved on. There would be nothing gained from sitting with women complaining about men—better to just go and talk to some.

Women aren’t the only ones making rash judgments, of course. As I made my way through the bar that evening, I heard similar complaints from the men. Some seemed to think that there must be “something wrong” with these women since they weren’t paired yet (I had to bite my tongue here. How a single adult can show up to a singles event and assume something’s wrong with everyone ELSE there because they’re single is beyond me). Of course, there were the equally ugly comments about women being too heavy or not hot enough.

One guy said he just wanted an average woman, because he considered himself average, but that people were a little generous in their descriptions of themselves online. He indicated a woman with a perfectly average figure and said, “I bet that woman calls herself average.” I said, That, my friend, is average. Nowhere on the invite did it say there’d be a cast of models and porn stars here. I’m not quite sure what people were expecting—or why they think they should be served Hollywood elite look-alikes just for showing up.

What You Expect, You’ll Get

There’s not a doubt in my mind that the people who came that night with their fears ratcheted way up and their expectations way down didn’t have fun, and likely left thinking it was a waste of a night. Which, by the way, is a very convenient way to keep your scarcity mentality-slash-insecurity stories in tact. Easy to keep believing the myth that “there’s no one out there for me.” I don’t buy into that, but the people who do find it to be true, every time.

I had a really great night. It wasn’t because there was some magic in the air—I believe that to a great extent we decide how good a night will be, and it doesn’t start with showing up and thinking, “OK, prove it to me that this is worth my time.” You have to make it worth your time. Here’s how.

How to Meet Your Next Average Stranger

Bear these in mind next time you head out.

Don’t form a coven. It’s great to have some girlfriends in tow when you hit up a social scene, but as soon as you turn in the wagons—and your back to everyone else—you’ve effectively sealed yourselves off from any nearby prospects. Man-bashing and complaining may be a fun way to meet new girlfriends, but I think it’s a cowardly way to spend an evening—not to mention unproductive. Stop talking about men and start talking to them.

DUDES: Standing around staring at a lady is, quite frankly, unnerving. If you have some wingmen on hand, invite a lady into a conversation, say to “settle a bet” about a disagreement you’re having (read: just made up), something to make her feel engaged, not stalked. Or, approach her with some normal conversation leads (not pick-up lines) handy so you can get to know her and not make her want to run for ze hills.

OR: Show up alone. I know this is unfathomable to some, and it requires some gumption, but I’m telling you, the upfront bravery has a bigger payoff. I came to this particular event by myself. One friend at the last minute did show up, but I was there long before her, and when she did arrive, she mingled separately. We spoke a few times, sent a few texts to see where the other one was and how she was doing, but we were not attached at the hip. Of course, there’s social pressure and not a small bit of dread to be there on your own, but that little bit of anxiety, and a big smile, will actually make you more likely to talk to people you don’t know—and more grateful for the conversation (thus a bit kinder in your approach).

Just aim to connect. If you put pressure on yourself to find a life partner, right here, tonight, you’re bound to fail. That’s not what you’re there to do. You’re there to connect—to interact with, learn about, and introduce yourself to people you know nothing about, and whom you might not even be attracted to. If you only talk to people who, on first glance, you’re sure you’d want to marry, you won’t be talking to too many people. Think of it as informational interviewing: You don’t necessarily want or need the job; you’re there to see what’s out there.

Assume the best. Nothing sours your outlook or your outcome by going in with a chip on your shoulder. You’ve been hurt? So has every single person in that room. If you go in with your dukes up, suspicious that every man (or woman) there is out to deceive, hurt, or outright reject you, it sends a message—and clear instructions on how to treat you. Challenge those assumptions. What if you assumed there was a lot about these guys you could love if you had a chance, that they have complex stories and big dreams, just like you? You’ll be far more open, that’s what.

Remember that average is the new hot. Granted, some people are just better looking than others. But as a rule, most people are…average. Personality, humor, and chemistry can transform someone you wouldn’t look twice at into someone you can’t bear to be without. It happens. But not if you don’t give that person a try and actually interact with them. An average or even good-looking guy can get ugly fast if he acts like an ass, but another guy can become more attractive if he’s kind, funny, engaged. Think of a face as a canvas that someone draws his or her personality on.

You already know that while looks are important, they aren’t everything. Most of the men I’ve had the strongest feelings for were not grade A hunks right out of an Abercrombie ad. The surprise of a growing attraction is the best part. More often than not, women fall for, pair up with, and enjoy mind-blowing sex with (and often marry) men who will never work as George Clooney’s body double.

Play the game. It’s a fact: Men like to hunt. As my own coach has said to me, hunting isn’t as fun when a deer jumps in front of the gun. And while I hate to use such violent, predatory imagery, it works here. While there’s nothing wrong with initiating conversation, especially at a social event, give a man some space to pursue you a bit, rather than a) try to stake him out and keep him cordoned off from other women or b) stalk him all night. Simply smile big, make eye contact, talk, laugh, touch him lightly on the arm from time to time. Compliment him. This is not rocket science, ladies. But it works.

Case in point: I spotted an attractive stranger that night, and made my way over to his general vicinity—so when the opportunity arose and he looked my way, I flashed a wide, open smile, the kind of smile that isn’t cursory but lasts a few beats longer, that says “I’d like to meet you.” He held out his hand and introduced himself. After speaking for a bit, I made it a point to give him some space—after all, if he thought I was worth talking to, he’d find me again. And he did: While I was talking with another gentleman, he swung by and handed me a drink, and kept walking. Well played.

Later, when I went to thank him for the drink, we were interrupted by a woman who said her friend wanted to meet him (ok, so yes, this guy was in fact strikingly handsome, no question). I stepped back and chatted with a few other people. After all, I don’t have dibs on this guy. Everyone should be able to talk to whomever they want—now is not the time to get proprietary.

“That was cool of you,” he remarked after the woman had left. “I’m glad you didn’t walk away.” We talked for the rest of the evening. He took my number and asked me out the next day.