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:
Jennifer: After a five-year relationship, she’s still getting used to the new rules of dating.
Matt: After a breakup, he’s burned out on dating apps.
Jennifer: Something sporty, like a Knicks game
Matt: Something low-key and quiet, like drinks somewhere divey
Jennifer: “He’s really tall. I went with a heel that was a little smaller. I remember thinking, I should have gone with the higher heel; he’s so much taller than me.”
Matt: “She was very outgoing and friendly; I could tell it wasn’t going to be a problem conversing. She was excited about the whole situation.”
Jennifer: “We’re the same age, so we talked about some things from the ’90s. It was like two friends hanging out, talking, enjoying the view.”
Matt: “There may have been some awkward pauses—my fault—but she maintained the conversation. There wasn’t a spark, but it was enjoyable.”
Jennifer: “We weren’t sure if we had to follow a certain menu, so we asked our waiter, and he had no idea what we were talking about. We just brushed it off.”
Matt: “Just a couple extended pauses in the conversation, thinking of what to say next. I wouldn’t say it was awkward at all; it was a very standard first date.”
Jennifer: “We walked to the subway together. He asked if I’d like to keep in touch. I said sure and gave him my number and a friendly hug goodbye.”
Matt: “Once we started eating and had a drink or two, we started to click a bit more. We left on a friendly note. I texted her later, but we haven’t texted each other since.”
Jennifer: ♥♥♥ “We talked about TV shows, and we had a lot of similarities, but it was just surface conversation. Nobody’s fault, just typical first-date talk.”
Matt: ♥♥♥♥ “The chemistry was fine, and she seemed like a great girl. I could see being friends, but I wouldn’t reach out for any romantic reason.”
Our daters went to One World Observatory (844-696-1776, 285 Fulton St)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.