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Let me tell you about my friend — we’ll call her Jessica — who came out as a lesbian after we graduated college. She’s confided in me that she has a really difficult time asking women out.
There are a few reasons Jess is shy. First, it’s downright nerve-racking to ask someone on a date (what if they say no?), and second, she’s not always 100 percent confident that the woman she wants to ask out is, in fact, a lesbian.
I try to be there for her and give any words of wisdom I think might help ease her mind, but the truth is, whether you’re a lesbian or straight, dating is tough.
If you’re looking to go cold-calling and ask out a woman you’ve never met, then make sure you’re at a place that’s conducive to doing just that.
Stay away from hunting clubs, chain restaurants and country concerts. Do go to lesbian bars, the gay and lesbian center in your town, join a local all-female sports team, or pick up your city’s gay newspaper and read the events page.
Now that you’ve found a woman you’re interested in, it’s time to strike up conversation. Starting with a compliment never hurts. Tell her you like her sweater, bracelet, hat, hairstyle, etc. And then follow up with an open-ended question like, “How long have you lived in town? Do you like it here?”
Even if you’re nervous, try you’re best to appear confident. Confidence is one of the sexiest qualities about a woman. Make eye contact with her and smile — women respond to this much better than just staring.
So the evening’s winding down, last call has been indicated and you and this gorgeous potential mate have been talking for well over an hour? There’s nothing left to do but ask her out.
Don’t be pushy. Nonchalantly give her your number and say, “I’ve really enjoyed hanging out with you. I’d love to get your number. If you’d prefer to call me, here’s my card. Let’s get together.”