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:
Robert: He’s not quite sure what he’s looking for yet and is exploring his options.
David: He’s only been out of the closet for two years and is new to the dating scene.
Robert: Something fun, like drinks before dancing—just don’t be wishy-washy when making plans
David: Something that fosters conversation, like a quiet dinner before a show or a walk
Robert: “I hugged him because it’s 2017 and people hug. When I first saw him, I thought, Okay, he doesn’t look like anyone I’ve ever dated. I could tell he was vegetarian by his outfit.”
David: “He’s actually not my physical type in any way, but he’s taller than I am, which is a plus. What caught my eye is that he definitely had his own vibe and this great smile.”
Robert: “We talked about a lot of stuff we liked, growing up, what we do—that was pretty easy. It wasn’t too awkward, but I don’t think there were any, like, sparks flying.”
David: “I don’t think there was a romantic vibe, but we had great chemistry at a friend level. He wasn’t standoffish or hard to talk to. The date was a lot of just figuring each other out.”
Robert: “I found out he was married before. I was like, Oh, so you’re a little bit older than I would’ve expected. I hope I didn’t wear my surprise on my face; I was just like, ‘Oh, okay.’ ”
David: “We were giving each other a goodbye hug, and then I realized we hadn’t exchanged numbers. He was like, ‘Wait, this is interrupting our normally scheduled programming.’ ”
Robert: “He doesn’t go out in the city a lot, so I was like, ‘If [you] ever want to explore bars...I could be your spirit guide.’ I don’t think he tried to go in for the kiss, which I was fine with.”
David: “I sent him a text saying I’d be interested in meeting him again if he was interested, and he responded that he would. But we haven’t set any concrete plans or anything.”
Robert: ♥♥♥ “He’s 31, has been married, lives in Jersey City and has a career. We’re in different places. If I were a Kardashian, [established] at such a young age, it’d be fine.”
David: ♥♥♥♥ “Even if we only stayed friends, I’m happy I had this experience. I think he’s got a great brain—he’s really smart—but I do feel like he’s quite a bit younger than me.”
Our daters went to The Wayfarer (212-691-0030, 101 W 57th St)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.