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:
Kathleen: She’s busy with work and has a hard time meeting other single people.
Lucas: He just moved to New York from Boston and hasn’t found the right person yet.
Kathleen: Hitting up a new restaurant or cocktail bar and then going on a walk
Lucas: A fun, interactive activity like pool or bowling
Kathleen: “I got there five minutes early. He still wasn’t there after half an hour, so I just ordered. I was scarfing down some bacon when he walked in. He was an hour late.”
Lucas: “The night started out rough. I got stuck on the train. I was surprised she was still there. I thought she’d throw a drink in my face, but she was super nice.”
Kathleen: “I don’t think either one of us would be categorized as flirts, but I was very comfortable. We have a similar sense of humor and ended up spending four hours together.”
Lucas: “I wouldn’t say there was romantic chemistry, but we had a great conversation. We talked a lot about work, music, sports... She was giving me shit that I’m a Red Sox fan.”
Kathleen: “We were talking sports, and I referred to Tommy John surgery, which is this elbow surgery a lot of pitchers get, as Jimmy John’s. He called me on it, and we laughed.”
Lucas: “When I got there an hour late.”
Kathleen: “He walked me to my car, and we exchanged numbers and hugged to say goodnight. We’ve texted a bit since then and said we’d both like to hang out again.”
Lucas: “We went and got coffee at a diner nearby and chatted some more. Then I walked her to her car. I totally see us hanging out again and grabbing a drink or something.”
Kathleen: ♥♥♥♥ “He’s a great addition to New York and would be someone I’d like to know. And the good thing about him being an hour late was that it was the ultimate icebreaker.”
Lucas: ♥♥♥ “It went great. It was a good time, nice evening. There were a lot of laughs. She’s a great person. Smart, funny and can hold a conversation.”
Our daters went to Lincoln Square Steak (208 W 70th St, 212-875-8600)
RECOMMENDED: See more Undateables
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