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:
John: He’s picky and hasn’t found the right person yet.
Kris: He expects a lot from others and is nervous about committing to something.
John: Something active like going for a walk or taking an art class
Kris: Having a drink and then doing something adventurous
John: “He was surprisingly cute. I was checking him out when I walked in. He seemed really nice right away, maybe nicer than I am. Not sure if that was just first-date manners.”
Kris: “I saw a cute guy in the corner and was hopeful it was him. I could tell he was nervous. Physically, he was my type, but he seemed a bit reserved at first.”
John: “We basically didn’t stop talking for three hours. I think I was kind of rambling, but he was actually really good at steering the conversation. I think he was interested.”
Kris: “You have some dates where it’s magnetic instantly, and then it fizzles out. But this was like a slow, building chemistry. I definitely think there was an attraction.”
John: “I don’t think there was any awkward moment. I guess just that he’s never been to Fire Island, so I wasn’t sure what his opinion of me would be, because I go often.”
Kris: “Dogs came up in the conversation, and he said that he didn’t really like them. I didn’t say anything at the time, but I actually have two small dogs.”
John: “At one point the manager came over, and we were like, ‘Oh. We’re still talking.’ So we got our stuff and left. We exchanged numbers outside the restaurant.”
Kris: “He sent me a really sweet text later that night that made me think he was actually interested. We’re currently slated for a second date this weekend.”
John: ♥♥♥♥ “I’d like to get to know him better. I’m curious if he might loosen up more if we meet again. He seemed really good and wholesome, and I’m not wholesome.”
Kris: : ♥♥♥♥ “I’m cautiously optimistic. I kind of felt like I was driving the conversation, but I think I was able to get under his layers. It was hard to tell if he was into me.”
Our daters went to Rossopomodoro (118 Greenwich Ave, 212-242-2310)
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