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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:
Asher: His work is an integral part of his life, so he's looking for someone with similar interests.
Alexandra: Is still holding out for the one.
Ideal date:
Asher: Bringing a pizza to Prospect Park and watching little league.
Alexandra: Live music, bar games and maybe a walk around the city.
First impression
Asher: “I had train trouble, so I came in late and frazzled. She was really cute—I don’t understand why she’d be undateable. She had a mousey voice, which I always like.”
Alexandra: “I could tell he was a nice Jewish boy. I’m Jewish, and my mom would yell at me for saying this, but that’s not really my type—I like taller, preppier guys.”
Chemistry
Asher: “We got more comfortable talking as the night went on. We kind of checked off everything you’re not supposed to talk about on dates—religion, politics, exes.”
Alexandra: “He asked me if I wanted to pick what the other person was drinking, which I thought was quirky and fun. He was easy to talk to, but I wasn’t feeling a romantic spark.”
Awkward Moment
Asher: “The restaurant was really nice, but I think they thought we were reviewing them. The staff kept coming over and asking us stuff while we were in the middle of conversation.”
Alexandra: “I was early, and while I was waiting, multiple members of the waitstaff came over. Each time, I thought it was my date, so I kept standing up to shake their hand!”
Afterward
Asher: “I asked if she’d like to go out again, and she said she’d been on a couple dates with another guy and didn’t want to juggle. It was refreshing that she was open.”
Alexandra: “He asked me on the spot if I wanted to go on a second date, and I didn’t. We rode the E train together one stop and had an awkward conversation.”
Verdict
Asher: ♥♥♥♥♥ “It says a fair amount about her that she was so honest. Even if we never see each other again, we had this fun, weird, interesting night.”
Alexandra: ♥♥♥ “He’s a great guy. He’ll make somebody extremely happy, but I didn’t feel an attraction. It was on my bucket list to do a truly blind date, so that was fun.”
Our daters went to Bar d'Eau at the Trump Soho (246 Spring St, 212-842-5500)
RECOMMENDED: Find more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.