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:
David: His relationships tend to lose momentum and fizzle out, and his career is his top priority.
Andy: Just moved here from Australia and doesn't want to rush into a relationship just for the sake of being in one.
David: Intellectual conversation at a nice, quiet restaurant over a bottle or two of wine.
Andy: Having a picnic and going on a hike upstate.
David: “His beard gave him a manly, rugged look. I noticed he had a bandage on his hand—I guess he’d sprained his finger. That was an easy conversation starter.”
Andy: “I liked the way he dressed—kind of lumberjacky. He came across as confident. We shook hands, but I’d broken a finger the night before, so that was a little awkward.”
David: “We come from different backgrounds and are in different fields, so that was interesting. Maybe it was the nerves, but I didn’t feel much chemistry.”
Andy: “The conversation flowed the whole time. He comes across as serious and career-driven. I’m sure he has a sense of humor, but it was hard to get him to crack a smile.”
David: “He was already waiting at the restaurant when I got there. I was five minutes early, but I guess he was 15 minutes early. The host just let him in.”
Andy: “He asked me my sign, and I hate that—it’s profiling and judging people. I went into a rant, but he was like, ‘I was just asking as a stepping point for conversation!’”
David: “We both got cabs, and I gave him my card. I have a dance gig coming up downtown this week, and he’s never seen ballet, so I invited him to it, and he’s actually coming.”
Andy: “We kissed lightly as we said goodbye—not like a make-out but a peck on the lips. I texted him saying I had a really good time and would get tickets to his show.”
David: ♥♥♥ “He’s an open-minded, smart, solid guy. If he texts me, I’d be down for a second date. You have to do that to really get to know someone.”
Andy: ♥♥♥ “He’s a great guy. Initially I didn’t feel sparks, but I’m definitely intrigued. I’d go on a second date if he texted me, but I don’t think I’d initiate.”
Our daters went to The Bar Room (117 E 60th St, 212-561-5523)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.