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:
Tanya: She has trouble finding someone she feels a connection with.
Max: He somewhat recently got out of a very long-term relationship.
Tanya: Drinks at a chill bar, then doing something out of the box like seeing a band neither of us have heard of
Max: Something outdoorsy like a hike in the Hudson Valley followed by wine and cheese
Tanya: “I thought he was really cute. It’s a blind date, so of course it was awkward at first, but we broke the ice pretty easily. He seemed really friendly and smart and my type.”
Max: “It came out pretty immediately that we both have a very dry sense of humor, which was good. It also came out that we both enjoy really horribly made movies.”
Tanya: “I definitely felt romantic chemistry. We have a lot in common. We swapped roommate horror stores. We talked bad dates. It was a really fun, casual conversation.”
Max: “The chemistry was pretty good. I don’t know if I have a type, but she was really nice. I collect vintage Hawaiian shirts, and we both showed up wearing Hawaiian prints.”
Tanya: “The server kept coming over, but we were talking so much we always forgot to decide what to order. It happened for the drinks and then a few times during the meal.”
Max: “While I was munching away on bread, she told me she has a very severe gluten allergy. I was like, ‘Oh, my bad. I don’t know if this precludes me from eating it....’ ”
Tanya: “We walked out together. When we got to the corner where we had to go different ways, he asked to exchange numbers, and I said absolutely. Then we kissed good night.”
Max: “We were the last people to leave the restaurant, and walked to where we were splitting off for subways. We’ve been texting a little since then.”
Tanya: ♥♥♥♥ “It was more fun than I thought it was going to be. I was a little terrified about who I would be matched up with, but I’m glad I did it. I’m down to see him again.”
Max: ♥♥♥♥ “It was such a funny experience being thrust in with someone you’ve never met and know nothing about. I think there’s a solid chance we’ll go out again.”
Our daters went to Tableside Italian Cook Shoppe (345 E 6th St, 646-852-6498)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email email@example.com.