Dating Expert: ‘I’m so shy. How do I ask her out?’

There is a beautiful woman at my climbing gym that I swear gives me extra long looks and smiles and seems to happen to always be climbing nearby.

 I am very shy, especially around a woman as beautiful and confident as her. I don’t even know if she is gay or  bisexual, but I really want to ask her out for a drink.

How do you met gay ladies outside of an obviously gay place like a Pride parade or gay bar?!

 I should mention that I am pretty feminine so there is no rainbow flag following me into a room or clear signal to her that I would be interested in women. Thanks!

 –Shy Girl

Dear Shy Girl,

While I haven’t spent a whole lot of time scoping babes, I have spent plenty of time in the gym lusting after a beautiful man (or 10) without ever having the balls to say “hi.”

 Sure, you don’t have balls of your own—in either sense—but that shouldn’t stop you from making a connection.

First things first: drop the labels. Femme or butch, it’s doesn’t matter what you are as long as you’re confident enough in yourself to make the first move.

 Just because you don’t instantly read as a lesbian on the prowl doesn’t mean you know anything about what this girl is looking for in someone else. Clearly you’re turned on by her confidence, and the sure-fire way to get her attention is to BE YOURSELF.

Nothing is sexier than someone who isn’t trying to be something they’re not.

Women are far more comfortable with the idea of being intimate friends with someone of the same sex than us guys—so whether or not she’s even interested in women, you can make a new friend who shares a common interest in climbing. Who knows what else you guys have in common that your shyness is keeping you from discovering?

 Start nice and easy with the friendship approach—you’re both in a climbing gym, so start a conversation about how long she’s been climbing and if she could offer you some tips. Once you’ve established some common ground, you can branch out to more exciting topics, and that’s when you’ll get a sense of her tastes, interests, and maybe even desires.

Whether it’s in the gym, at the bar, on the subway, or at the next office party, just strike up a conversation with someone you’re curious about getting to know—on a subject you both share obvious interests in— and let it go from there. Think of dating as the search for a friend with some meaningful canoodling—as long as everything starts from a honest, confident friendship there’s no limit to where it can grow.

Even if she’s not looking for anything more than a friend to go rock climbing with, you have a very sexy new friend!

All you have to do is say “hi.”  And let’s be honest, she’s a hottie in a rock climbing gym—the odds are on your side!

Jonathan Lovitz, a Setup Squad wingman, is a true southern boy who loves sweet tea and sandals all year long. There’s nothing he loves more than soaking-in all that NYC has to offer, from the incredible museums to the unbeatable gay nightlife to playtime in Central Park with his French Bulldog, Potato.