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:
Katie: She thinks apps should be for dinner not dating.
Sam: He’s too funny and interesting for most people, and that can come off as threatening.
Katie: Walking around, talking and stopping in a few bars
Sam: Drinks and conversation outdoors
Katie: “I got there first. He came over to the table, I stood up, and we shook hands. He gave off a not-caring, kind-of-detached vibe. My guess was that he was nervous.”
Sam: “It took the host about five minutes to find the reservation. Once they sorted it out, they brought me over. Right away, I could tell she was really friendly, just not my type.”
Katie: “I thought maybe he had read that pickup artist book and was trying to neg me. At one point, he asked me the name of my improv group and then said it was a bad name.”
Sam: “She said she’d tried to watch Cry-Baby many times but couldn’t finish it. That’s a deal breaker for me. I don’t think I could ever date someone who doesn’t like that film.”
Katie: “I told him I moved three months ago, and he said that I’d meant to say 15 months ago. I was like, ‘No. I moved this past May.’ And he told me my math didn’t add up.”
Sam: “I don’t remember anything being awkward—just breaking the ice at the beginning, but that always is [the case]. You never know if you should shake hands, hug or what.”
Katie: “He looked at his watch and was like, ‘I have to go.’ I said I was going to leave a tip, and he just walked away and left. He was waiting for me outside, and we said goodbye.”
Sam: “I got dessert. I think she had a whiskey. Maybe that’s her version of dessert. Outside, I asked how I could find her shows, and she asked how she could find mine.”
Katie: ♥♥ “I learned a lot about myself and how I am on dates. I’m mostly pleasant during them, but my real assessment of the night comes after I leave.”
Sam: ♥♥♥♥ “We got along, we had a great conversation, we laughed a bunch, but there was nothing really there for me. There needs to be a little heat, a little something.”
Our daters went to Marlow Bistro (1018 Amsterdam Ave, 212-662-9020)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.