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:
Michelle: She recently moved back to New York from L.A. and hasn’t met new people.
Tim: He’s usually too picky and then acts too enthusiastic when he finds someone he actually does like.
Michelle: Dinner followed by a dive bar with arcade games
Tim: Citi Biking around and then having a picnic
Michelle: “He was really cute. He walked in, and I noticed that he had tattoos, which I like. I was like, Oh, my god, thank God he’s cute. He seemed really nice and easygoing.”
Tim: “She was pretty, but she wasn’t really my type. I normally go for goofier, more eccentric people, and she seemed very Manhattan and put-together. But still fun.”
Michelle: “I feel like there was romantic chemistry. I was touching him. There was good eye contact. I asked him the story of his tattoo, but I really just wanted to touch his arm.”
Tim: “I had a lot of fun but didn’t really feel a romantic vibe. I knew pretty early on that I wasn’t interested romantically, but I was having a good time hanging out with her.”
Michelle: “His dad kept texting him asking how the date was going. At one point, he suggested we get some whipped cream and an umbrella. I was like, ‘What does that mean?’ ”
Tim: “As the meal was wrapping up, I was like, ‘I guess we should hit the bricks.’ I think she was taken aback. It seemed like she expected we might go somewhere else.”
Michelle: “We stood outside the restaurant and exchanged numbers. I suggested keeping the night going, but he was jet-lagged. There was a kiss, and then we said goodbye.”
Tim: “I went in for a hug. It felt like she held it for a long time, and when I pulled back it was like our faces were right next to each other, and then we made out. It was great.”
Michelle: ♥♥♥♥ “It was one of the better first dates I’ve ever had. Usually it’s not so easy and comfortable, plus he’s just so cute. It was a really fun night. Good food, great evening.”
Tim: ♥♥♥♥ “I had a great time, and she was a great person. It was super easy to talk to her. I just wasn’t interested in her romantically or seriously.”
Our daters went to Pig Bleecker (155 Bleecker St)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.