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Got Game? Expert Tips For Connecting After Dark

Posted by Karyn Polewaczyk  May 23, 2013 03:00 PM

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402431_10150609444772597_662133652_n.jpg(Photo credit: Chad Griffith)

Imagine this: it’s Friday night, and you’re out with your friends at a local watering hole. You spot an attractive stranger from across the room, and briefly lock eyes. You report your findings to your group and reach a general consensus: he is, indeed, cute, and you should definitely introduce yourself.

Except, maybe you’re shy. Or maybe you’re not sure if he was looking at you, or if he was looking at the person standing behind you. What if he’s got a girlfriend? And how embarrassed will you feel if you have to slink back to your friends without a digit-clad cocktail napkin in hand? Slowly but surely, the opportunity to say hello passes, and the next day, you kick yourself for holding back.

As I mentioned in last week’s post, there’s a slew of new apps designed to solve the availability equation, where, depending upon which service you choose, you can vet nearby prospects’ interest, and, if it’s mutual connect accordingly. But is that really connecting, or will these programs drive us further apart?

I spoke about the matter with relationship expert and coach, Terri Trespicio. (You may recognize her from the cover of Boston magazine, where she was featured in its Single By Choice article last year.) Connecting with strangers is not just for the brazen, folks. Read on for her tips on how to make approaching strangers easier, and why bouncing back from rejection is part of the (dating) game.

What are some of the mistakes you’ve seen when it comes to approaching people at bars (or in clubs, restaurants, etc.)? And how can it be fixed?

It depends on the expectations we have about who should do the approaching and by whom. Approaching a stranger is the single bravest thing you can do. In fact, if you are willing to make an approach, you are my hero or heroine.The idea that you have to have a come-on line is nonsense. Obviously if you’re approaching someone, you’re interested, so you don’t have to be cheesy or make a game out of it. You just go up to someone and say hello. Even if that person isn’t available per se, she (or he) will be flattered because who wouldn’t be?

And it’s not about the approach; it’s whether you’re enabling the approach. If you want to meet people, go out with one or two people, and make sure you’re facing toward the crowd, making eye contact with and smiling at people who happen by. You have to make yourself seem like a friendly threshold if you want someone to cross it.

In a popular post I wrote, I tell women that they don’t have to charge up to a dude in an unnatural way; rather, get yourself in his immediate vicinity, by “accident.” Smile and strike up conversation. I call it “happening to” because it’s better than “hitting on” which sounds so awkward and lame. No hitting. Think happening. Being near and striking up conversation with someone. It’s how you show you’re interested, and a gentler, less hard-charging way to connect with someone who interests you.

A lot of your suggestions on how to "happen" start inside, with confidence. How can a person boost their own levels without the aid of liquid courage? (I like getting ready to feel-good music, like Beyoncé, for example.)

First, recognize that rejection is part of the game. Shift your goal: It isn’t to race through the dating maze and land The One without ever getting hurt. Guys know going into it they’re going to be rejected a certain percentage of the time. They keep going until they get a 'Yes' from someone. Women tend to reach out tentatively, and if they don’t receive an overwhelmingly positive response back, they retreat, assume it was a mistake, and that they shouldn’t have done it. Wrong. Confidence comes with practice, and from not letting one bad interaction, date, what have you, dictate your decisions or define your life.

By all means—listen to great music before you go out. Go for a run. Do things that feel good to you. But all the stilettos in the world will never give you a sense of worth—they can only accent what’s there. The core of confidence comes from knowing that this one night, this one date, this one person is not the end of you or the be-all, end-all of your love life. When you realize everything’s not hinging on any one thing, you can roll with it and actually enjoy what happens, instead of worrying it should have happened a different way.

Is there a difference in approaching a stranger if you're out with friends versus alone? (And is one scenario easier than the other, when it comes to the actual approach?)

Yes. When you’re with a group of girlfriends, you’re not likely to meet a guy. I laugh when women go out in teams. Who are you playing against tonight? Because you win: No one’s going to try to take you down. I have a girlfriend who has been my wingwoman—and when we’re out, we don’t hang on each other all night—we separate, we circulate, we check in with each other. And at some point in the evening, we introduce each other to the people we just met.

Going out alone can seem terrifying. Try it. Go out to dinner, sit at the bar, chat with the bartender and bar patrons, and enjoy a social night among strangers. It can be really fun. No expectations. I think it’s a wonderful thing to do regularly to remind you that you’re quite capable of talking to people you don’t know. Next birthday party or book launch or conference you attend, go alone and introduce yourself to people, get a drink, walk around. You’re more likely to meet folks if you show up at an event alone than if you bring a guest. Don’t think of yourself as some loser who doesn’t know anyone, but the person people want to talk to.

Finally, are these suggestions just as relevant for men as they are for women? Can the tables turn, or do traditional rules apply, where the guy should take charge?

In our culture, and many others, men do the initiating, and women decline or accept. When a man approaches you, you have a choice. But as I said earlier, the idea that a woman can’t initiate is nuts. As a woman, I’m not trying to out-man a man. What you do is set the stage for a man to feel comfortable approaching. Your body language, your facial expression—how do you read to a room full of a strangers? Ask a friend to give you an across-the-room review. What does your energy say? Is it, “Don’t bother, I’m already annoyed with you” or more like, “Hey, I’d love to talk"? It’s a two-way street. The game is not to try to cajole someone into paying attention to you. It’s about creating the conditions for connection to occur, and being accountable for the actions that take you there, male or female.

Terri Trespicio is a relationship expert and coach, and has contributed to The Date Report, Jezebel, Marie Claire, and Boston Common magazine. Visit her at and follow her on Twitter @TerriT.

This blog is not written or edited by or the Boston Globe.
The author is solely responsible for the content.

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About this blog

Karyn Polewaczyk lives and writes in Boston, and believes that heading out into that good night, like any adventure, begins with the first step. Let's Go Out is a conversation about dating and nightlife in our notoriously chilly city, with first-hand tips from the trenches. Karyn's writing, which focuses largely on women's lifestyle topics, has appeared in the Weekly Dig, Jezebel, xoJane, Northshore Magazine and, among others. Follow her on Twitter at @KarynPolewaczyk.

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