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:
Drew: Doesn’t want to be in a relationship just for the sake of having one and isn’t willing to settle
Jen: Is still waiting for the right person to have an adventure with
Drew: Dinner followed by drinks at a dive bar
Jen: Dollar pizza and the park
Drew: “We started chatting and ordering as soon as she arrived. She was very attractive and dressed well. She had on a dress and heels, but I was in a T-shirt and jeans.”
Jen: “We shook hands—maybe we should have hugged, but that seemed more natural. He had a nice smile and positive energy. He seemed excited to be there.”
Drew: “It was like a regular awkward first date, like where are you from, how long have you been in New York type of things. I talk a lot when I’m nervous. She was a good listener.”
Jen: “He told a lot of stories—I learned a lot about him. He said he was nervous and apologized for speaking a lot, but I don’t think he asked one question about me.”
Drew: “The staff came over and placed down two plates, then realized we hadn’t even ordered yet, looked at us and took them away. I didn’t ask why."
Jen: “He started the conversation by telling me that an ex signed him up for this and they still talk. Those things come up, but maybe they shouldn’t in the first five minutes.”
Drew: “We walked to the corner, and when a cab pulled up, I helped her in and sent her off. It was a very benign goodbye. I didn’t really feel the urgency to see her again.”
Jen: “I hailed a cab, hugged him goodbye, said, ‘It was nice to meet you,’ and that was it. I wasn’t surprised he didn’t ask for my number. I would have been fine either way.”
Drew: ♥♥♥ “She was sweet and pretty, but there wasn’t that spark you look for. I like someone with a little more spunk, someone feisty and uncontrollable.”
Jen: ♥♥♥♥ “He was nice, but the conversation felt like one person hitting a ball against a wall. He’ll make somebody happy, but I don’t think I’m that person.”
Our daters went to Beauty & Essex (146 Essex St, 212-614-0146)
RECOMMENDED: Find more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.