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:
Caitlin: She hasn’t found someone she thinks is worth settling down for.
Cameron: He’s a bit of a scatterbrain who’s not ready to focus on commitment.
Caitlin: Something spontaneous, like an arty adventure around the city
Cameron: Drinks (to loosen the mood) somewhere lively, like a pub or rooftop bar
Caitlin: “He was almost 30 minutes late; I was convinced I was stood up. When he got there, he had this look on his face, like ‘I’m so sorry.’ We cracked some jokes and got to talking.”
Cameron: “I was rushing because I ended up being a little bit late. When I got there, she was down-to-earth, chill and cool. We could talk about anything.”
Caitlin: “We talked a lot about sports and found out we frequent a lot of the same bars. I felt like he was my bud or my comrade; I wasn’t getting the vibe.”
Cameron: “It was really easy; I could tell she’s kind of loud like I am. Both of us could go into any situation, and it wouldn’t be awful no matter who we’re talking to.”
Caitlin: “It flowed really well. [But] my biggest pet peeve: I don’t want to see your cell phone on our first date. You should show me that you’re interested in me.”
Cameron: “There were little moments, like how I wanted to leave a tip, but I had to go down to the ATM to get cash. Nothing too crazy, just funny jokes.”
Caitlin: “We left and went to another bar. I was exhausted, so I caught an Uber home. I think he went out after. He texted me later that night, which was nice.”
Cameron: “We left the bar, and she asked for my number. We started texting for the next couple of days. I wouldn’t mind if she hit me up for something cool to do.”
Caitlin: ♥♥♥♥ “Honestly, he seems like he has a little growing up to do, like he parties a bit too much. I hope we hang out again—strictly in a friend capacity.”
Cameron: ♥♥♥♥ “She’s never going to go on a bad date; she just has that personality. Same with me. If she wanted to hang out again, I would, but who knows?”
Our daters went to Bar SixtyFive (30 Rockefeller Plaza, 65th floor, 212-632-5000)
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