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Each week, we take two New Yorkers who swear they're totally undateable, and put our matchmaking skills to the test. Afterward, we find out what went well on their date, and what went horribly, horribly wrong.
Why they're single:
Lindsay: Is picky about her type—femme lesbians can be hard to find—and isn’t in the lesbian-community cliques
Naimah: Feels like she’s awkward and doesn’t know how to approach girls
Ideal date:
Lindsay: Drinking whiskey or good beer at a nice bar and then walking around a park
Naimah: Some daytime drinking, maybe at brunch, then wandering around the city and seeing cool things
THE DATE
First impression
Lindsay: “She looked like a cool, chill person. I liked her outfit. But I tend to like very girly girls, and she wasn’t particularly that type. We shook hands first and then hugged.”
Naimah: “When I got there, she was already sitting down. She looks very gay, which is a positive. I don’t have a type, but she was cute and seemed super chill. I love chill.”
Chemistry
Lindsay: “There wasn’t romantic chemistry, but we definitely connected. We’re in different industries but have similar philosophies about doing what we’re passionate about.”
Naimah: “Neither of us was really flirting. We settled into a hang-out-and-be-bros type of situation. I asked a lot of questions—I was interested in hearing what she had to say.”
Awkward Moment
Lindsay: “These two tipsy women came up from the bathroom and thought we were the coat check. I was like, ‘Sorry ladies, I don’t know what you’re looking for.’ It was strange.”
Naimah: “When we got the check, we realized that we’d eaten and drunk a lot. I think both of us were shocked by it. It was like, Damn, we definitely did that.”
Afterward
Lindsay: “We sat outside for a while chatting on a stoop, and then it was getting cold, so we went down to the subway. There was a hug and a ‘Let’s meet up again sometime.’”
Naimah: “In the train station, I was like, ‘You got a Facebook?’ So we’re Facebook friends now. I suck at texting, so if I actually want to talk to you, Facebook is the best option.”
Verdict
Lindsay: ♥♥♥♥ “As a friend date, it was pretty good. She’s a cool, smart person who I could definitely talk to. It wasn’t romantic, but that was okay. I wasn’t disappointed.”
Naimah: ♥♥♥♥ “I don’t see romantic potential, but I want to hang out with her. She’s a genuinely interesting person. It was one of my better dates but felt like a hangout sesh.”
Our daters went to Añejo (301 Church St, 212-920-6270)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.