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:
Alejandra: She over schedules herself and doesn’t make time for dating.
Ryan: He’s at the point where he’d rather be single than settled
Alejandra: Jumping on a plane and traveling to another country
Ryan: Going to a concert or a Broadway show and then grabbing drinks outdoors.
Alejandra: “He was very cute, and we have a lot in common. We both like to travel, we both like cauliflower, he likes to cook.… He seemed family-oriented and was a good listener.”
Ryan: “She was super nice, just not the type of girl I usually date—not really my type. But she was very personable, friendly, and there was never a lull in the conversation.”
Alejandra: “He was pretty interested in the work that I do with nonprofits. I felt that we vibed really well. Also, he smokes his own cheese, which I thought was impressive.”
Ryan: “She’s a big talker, so I was mainly listening and asking questions. I think I heard her whole life story, but I still don’t think she knows anything about me.”
Alejandra: “He said he didn’t really eat carbs, and my face kind of fell—it’s just one of those things I can’t really control. But he did try some of my lobster mac and cheese.”
Ryan: “Our table was by a window that looked out onto the [Rockefeller Center] ice rink, and people kept slamming into the glass or wiping out right in front of us.”
Alejandra: “We’d both been talking a lot and had to work the next day, so we mutually decided to call it a night. I gave him a rain check on ice-skating and we hugged goodbye.”
Ryan: “We were there for four hours, and it was kind of slow going because there was a lot of talking between courses. Then we walked to her stop and exchanged numbers.”
Alejandra: ♥♥♥♥ “It went great. I had a great time and I hope to see him again. He was really nice, cultured, well-traveled and seemed down-to-earth but also successful.”
Ryan: ♥♥ “If it was a date I was paying for, I probably would have left. But it was an entertaining night. She’s a cool person; there was just no romantic connection.”
Our daters went to The Sea Grill (212-332-7610, 19 W 49th St)
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