Meet the Undateables: Jason and Billy

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test



Why they’re single:
Jason: He’s picky and has read too many 19th-century German romance novels.
Billy: He’d rather do a million things than pursue a guy who’s emotionally unavailable.

Ideal date:
Jason: An art exhibit, followed by a long dinner
Billy: Meeting up for a drink, then taking a stroll around the city


First impression
Jason: “I walked in and I thought he was really cute, really nice. He seemed like a very easygoing guy, pretty funny. I didn’t feel awkward or anxious at all.”
Billy: “I was 15 minutes early because I just assumed the subways wouldn’t be working. He had a really great energy. I thought he was lovely, thoughtful and intelligent.”

Jason: “I think there was romantic chemistry. It’s hard to tell on a first date, but there was nonstop talking. And we were interested in the things we were talking about.”
Billy: “There was definitely chemistry, but I don’t know if it was romantic. It would probably take a few more dates. I think both of us could have a conversation with a pole.”

Awkward Moment
Jason: “I found two Altoids in my pocket and offered him one. Then I was like, ‘Oh, I hope you don’t think it’s gross that I’m someone who gave you a mint from my coat pocket.’ ”
Billy: “About 10 minutes into the date, he mentioned his best friend, and I realized that I went on a couple of date with him. So that was a little bit awkward."

Jason: “After dinner, we went to a nearby bar—Flower Shop—for a few drinks. Then, we took the train uptown. I walked him to his apartment, and we had a little kiss on the street.”
Billy: “We took the subway home, and he walked me to my door, which was nice. We said goodbye on the corner by my building and friended each other on Facebook.”

Jason: ♥♥♥♥♥ “We exchanged numbers and made plans to get dim sum. It went great. The night was excellent fun—it turned out better than I thought it would.”
Billy: ♥♥♥♥ “My gut was to say five stars, but, at the same time, I wasn’t sure if there was romantic chemistry or if we were vibing as friends. But it was a very stellar date.”

Our daters went to Bar Belly (917-488-0943, 14 Orchard Street)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email