How (Not) to Talk to Strangers

Courtesy of FreeDigitalPhotos.netCourtesy of

I recently attended a singles event in Manhattan sponsored by an online dating site. 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). I asked the ringleader what she thought. In one facial twitch, dismissed the crowd of men outright. Why? "Eh," she said. Too old, not goodlooking enough, not my type. "Well, we don't see anyone worth talking to, so in a bit, we're thinking of going to a bar down the street."

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).

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. 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.


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. Stop talking about men and start talking to them.

DUDES: Standing around staring at a lady is, quite frankly, unnerving. Start a conversation, get her engaged in a topic so you can get to know her without freaking her out.

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 went alone, but a friend of mine showed up later-tho we did not hole up together. We were there to meet people. When you're alone, 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-even to people you're not necessarily 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.

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.

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. 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. The surprise of a growing attraction is the best part.

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. Smile, laugh, compliment him, move on. He'll be back. This is not rocket science.

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 stepped away. Later, while I was talking with another gentleman, he swung by and handed me a drink, and kept walking. Well played.

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.

"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.

Terri Trespicio is a writer, speaker, expert, and coach. She's the creator of Visit her at