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.

Photograph: Kelsey Dubinsky

Why they're single:

Alyssa: She’s picky and has trouble finding someone with a good sense of humor.

Billy: He has a busy schedule, and it takes more than just a beautiful woman to turn his head

Ideal date:

Alyssa: Happy hour at a bar, or something very noncommittal.

Billy: A picnic in Central Park

THE DATE

First impression

Alyssa: “I didn’t want to be that girl who’s late, and I was trying really hard, but I was about three minutes late. He stood up, and we hugged. He was really nice and charming.”

Billy: “She was about five minutes late, which annoyed the shit out of me. As soon as she walked into the room, I knew she wasn’t the girl for me. She didn’t have the goods.”

Chemistry

Alyssa: “He’s an actor, and that’s totally uncharted territory for me. I like a really stable job in a significant other. But the conversation was very friendly. He did a lot of the talking.”

Billy: “Whether I was attracted to her or not, I still had to sit there for two hours and be a gentleman. We had a nice conversation. She complimented me many times.”

Awkward Moment

Alyssa: “A couple of times he told me not to be nervous. I wasn’t nervous, but that made me second-guess myself and get in my head. And then the conversation stalled.”

Billy: “She ordered her filet mignon well done. The waiter just looked at me, and I looked at the waiter. I was like, ‘Live your life, but this is not Outback Steakhouse, girl.’ ”

Afterward

Alyssa: “We got a little ice cream afterward, which was awesome. We both gabbed about the fact that we really respect a place that will give you a macaron with your ice cream.”

Billy: “I was trying to be nice and end the date, but the waiter was like, ‘Do you want some ice cream?’ and she was like, ‘Yay! Ice cream!’ So that was another 20 minutes.”

Verdict

Alyssa: ♥♥♥ “We left the restaurant, walked to the subway and said goodbye. I’m really glad that I met him; he was really interesting and cool. But I got more of a friend vibe.”

Billy: ♥ “There was nothing drawing me in. She was very sweet, always smiling, always bubbly. But I feel like I took two hours of my time and kind of just burned it.”

Our daters went to Greenwich Steakhouse (62 Greenwich Ave, 212-553-5000)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email undateable@timeout.com.