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:
Amelia: Dating in New York moves so quickly, and it’s hard to find someone who wants to settle down.
Matt: Like U2, he still hasn’t found what he’s looking for.
Amelia: Dinner and cocktails at a nice restaurant, then walking around the city
Matt: A nontraditional adventure like listening to some music in a park or a picnic on a pier
Amelia: “He was a little bit late, but it wasn’t a big deal for me. He seemed like a nice guy. He was outgoing and easy to talk to and get along with.”
Matt: “I was fresh off a weekend of Phish shows, and I rode my bike there—I was struggling. She was outgoing and forgave me for sweating a lot.”
Amelia: “We walked around to different food trucks and got the basic stuff out of the way. The conversation never stopped, but for me it was a more friendly vibe.”
Matt: “There was no shortage of conversation or laughter. Once she told me about her weekend adventures and I shared mine, I thought, This chick is cool and she can hang.”
Amelia: “Because he was late, we missed the first steps in the cumbia dance lesson. Neither of us were on the beat, but I thought it was cool he wanted to give it a go anyway.”
Matt: “We chatted for maybe three minutes prior to hitting the dance floor. We missed the basics, and they were teaching us how to spin your partner. We laughed it off.”
Amelia: “We went for a bike ride for 30 minutes, then I took an Uber home. He didn’t ask for my number. I think he was scared to. He went in for a kiss—just a small peck.”
Matt: “I got her a Citi Bike, and we biked down the West Side. Her Uber arrived suddenly, so we had a quick goodbye, and I was like, Oh, shit, I don’t even have her number.”
Amelia: ♥♥♥ “He’s a cool person and it was a fun date, but I don’t think I was attracted to him. I’d be totally down to hang out again, but I don’t think I’d be into him like that.”
Matt: ♥♥♥ “I don’t know if I felt a crazy romantic connection, but we had a fun adventure. Can you ask her if I can have her number?”
Our daters went to Midsummer Night Swing at Lincoln Center (Damrosch Park (at Lincoln Center), 62nd St between Amsterdam and Columbus Aves, 212-875-5375)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.