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:
Coulby: Just recently started to focus on dating and getting himself out there
Joe: Likes to be in control and has spent a lot of time working on himself and letting go of old habits
Coulby: Dinner then something fun and interactive like bowling or minigolf
Joe: Grabbing beers or cocktails at a low-key dive bar
Coulby: “My initial feelings were, Oh, phew, he doesn’t look crazy. He went in for a handshake, but I was like, ‘No, its okay, we can hug.’ It was really chill from that point forward.”
Joe: “He’s not the type I usually go for—I like boys with beer bellies and beards. He’s a little smaller and thinner. I think I just automatically friend-zoned him.”
Coulby: “We laughed a lot—the conversation never felt flat. I was trying to really stay in the moment and not overthink anything, but it wasn’t romantic for me.”
Joe: “We just had surface conversation that you’d have with anyone you meet at a bar. After the first 10 minutes, I was thinking, Mmm, no. I didn’t feel romantically connected.”
Coulby: “He hadn’t bowled since he was 14, but he was fantastic. I kept trying different techniques and not nailing it. He took pictures of his great score next to my terrible one.”
Joe: “As I was walking in, a guy waved. I was like, This must be him! I said, ‘Hey!’ Then someone walked up behind me, and I realized he was just some guy waiting for his friend.”
Coulby: “He said, ‘Text me to let me know you made it home safe,’ but when I got home, he’d already texted, saying, ‘I had a great time.’ I said I had a nice time too, and that was that.”
Joe: “We were taking the same train, so I led us to the station because he’d never really been to Brooklyn. He was like, ‘Oh, we’re in Williamsburg?’ That was shocking to me."
Coulby: ♥♥♥♥ “It was a great time. There was no major turnoff. Then the ‘but’ comes in—and I feel bad—but I don’t want to go on another date with this guy. It’s just my instinct.”
Joe: ♥♥♥ “He was a really cool guy. I’m not into him like that, but if he wanted to grab a drink or see a show, I might do that. But I probably wouldn’t be the first to reach out.”
Our daters went to Brooklyn Bowl (61 Wythe Ave, 718-963-3369)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email email@example.com.