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:
Diamond: She has high standards and is ready for a self-sufficient, career-oriented guy.
Anthony: He’s a picky Tinder veteran who works too much.
Diamond: Good conversation, preferably over a meal at a place with lots of menu options, like a diner
Anthony: Something not too complicated, like drinks to see if there’s chemistry before moving on to dinner
Diamond: “I got there first, and then Anthony came and he put two and two together. He was well dressed, but he’s short—and I’m 5'8".”
Anthony: “I’ve never been on a blind date. I got there five minutes late and saw someone I thought might be her, and I was right. Objectively, she was pretty cute.”
Diamond: “He was like a friend that I knew from high school. We had a good rapport but it was really beginner questions like, ‘Where do your parents live?’ ”
Anthony: “About 20 minutes in, it felt like we were just having a regular conversation. I’m generally pretty sarcastic when I flirt; it didn’t hit with her. She’s more talkative and brash.”
Diamond: “The place was nice, but they didn’t have our reservation. We were like, ‘What should we do?’ But because we were both in the same situation, it was easy to talk to him.”
Anthony: “She went to the bathroom and said that someone she knew saw her from outside the door. I didn’t know how to react, so I joked: ‘You must have a world-famous crotch.’ ”
Diamond: “We walked to the nearest train station. I got on one train and he got on his. He had mentioned he hadn’t been in a long-term relationship, so I told him, ‘I hope you find love.’”
Anthony: “We ended up splitting the bill. I thought she was going to ask for my number, and that made me nervous. I knew there wasn’t going to be a kiss.”
Diamond: ♥♥♥♥ “I don’t regret it. He’s good at giving advice and very thoughtful. I’d go out with him again, but it would be a friendly outing. I didn’t think he was weird.”
Anthony: ♥♥ “It wasn’t uncomfortable, but I’ve been on enough first dates to know that we didn’t have as many similarities as two people on a good first date.”
Our daters went to Ribalta (48 E 12th St, 212-777-7781)
RECOMMENDED: See more Undateables
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