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:
Jermaine: He’s an outgoing guy, but intimacy makes him nervous.
Kaine: Something low-pressure that could potentially lead to more—like a boozy brunch
Jermaine: An experience that sparks conversation, like a walk around a new neighborhood or watching a political film
Kaine: “He got to the restaurant before me. He seemed approachable and welcoming. I thought he looked quite friendly.”
Jermaine: “He came in with a bright smile, and we shook hands, sort of hugged. I got a warm feeling from him; he seemed like a cool guy. It wasn’t love at first sight. He just seemed nice.”
Kaine: “We kind of ran out of things to talk about toward the end of the date, so there probably wasn’t much chemistry. We spoke about New York in general.”
Jermaine: “I didn’t feel sexual or romantic chemistry, but I definitely felt he was somebody I could get to know and hang out with. We talked a lot: music, politics, food, culture.”
Kaine: “When I walked in, I fell quite loudly. I didn’t realize he was actually sitting in the back room, so he didn’t see any of that, but the waiter mentioned it, so it was revealed.”
Jermaine: “We both ordered the pad thai, but they only brought one out, so we had to wait another 10 minutes for them to cook another pad thai for him. That was the only hiccup.”
Kaine: “We left the restaurant and headed in separate directions. There was no initiation on either part to swap details. It was well paced as we were eating; it ended organically, I guess.”
Jermaine: “It was his best friend in Australia’s birthday, so he wanted to get home to call his friend. We didn’t exchange numbers; I forgot about it until after the fact.”
Kaine♥♥♥ “It wasn’t especially memorable except that I fell over. If it was four or five stars, I think we would’ve made an effort to ask for each other’s number.”
Jermaine♥♥♥♥ “He seemed like a genuinely good person, so that made it enjoyable. But unfortunately, I don’t think it was a romance connection. I wasn’t let down or anything.”
Our daters went to Pinto Garden (212-366-5455, 117 W 10th St)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.