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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:
Lana: Isn’t looking to be in a relationship—her career, friendships and family trump seeking a boyfriend.
Sanjay: Doesn’t know what he’s looking for and thinks he might be broken.
Ideal date:
Lana: Going to a sporting event or concert, then grabbing dinner and drinks.
Sanjay: Going on a hike or taking a walk on the High Line.
THE DATE
First impression
Lana: “He was about 25 minutes late, so he rushed through the door and looked a little frazzled. He seemed like a nice guy—he was well dressed and polite.”
Sanjay: “I was driving, and there was a mini riot that blocked off the street, so I was 24 minutes late. I felt really bad. She was very respectful and sweet.”
Chemistry
Lana: “There was a nice flow to the conversation, but we’re completely different. He said he’d never been to a concert or sporting event and had no desire to.”
Sanjay: “There were no gaps in the conversation, and I don’t think I said anything that made her angry. We found out we had two mutual friends—small world!”
Awkward Moment
Lana: “I was ready to leave after five more minutes of waiting for him to show up—I guess he drove and got stuck behind a protest. He was extremely apologetic.”
Sanjay: “I think there was an open mic night, so the bar turned into a rap club. People were just, like, grinding on each other. We commented on it quite a bit.”
Afterward
Lana: “He walked me to my train, which was really nice. We’d exchanged business cards during the meal, so we just hugged and said good night.”
Sanjay: “We were there a long time. I don’t care if it’s my soul mate—I don’t have anything else to say after three hours. I asked her to text me when she got home. She did not.”
Verdict
Lana: ♥♥♥♥ “I really had a good time but not in a romantic way. I could totally hang out with him in the future as friends but probably wouldn’t initiate it.”
Sanjay: ♥♥♥♥♥ “The date went very well. She did everything right, but I felt not a single romantic spark. It’s not her fault—I haven’t felt one in five years.”
Our daters went to Manhattan Brew & Vine (998 Columbus Ave, 646-964-4091)
RECOMMENDED: Find more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.