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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:
Danielle: Broke up with a serious boyfriend after freshman year and has been nervous about putting herself out there ever since.
Ben: Is very outgoing but bad at making a move, so ends up getting stuck in the friend zone.
Ideal date:
Danielle: Something outdoorsy, like hiking or mountain biking.
Ben: Going out to a nice seafood restaurant and then taking a romantic walk on the beach.
THE DATE
First impression
Danielle: “I was 30 minutes late because the trains were awful, so I felt bad. He was cuter than I was expecting. He was friendly—he’d already made friends with the bouncer.”
Ben: “She was 45 minutes late but was very apologetic. I was glad she was normal—I mean that in a great way. But she wasn’t Jewish. My mother wouldn’t like that.”
Chemistry
Danielle: “He was sweet. He kept conversation flowing, and there weren’t awkward silences. As the night went on, we became more ourselves, but I’m not sure if there’s a connection yet.”
Ben: “I didn’t feel anything romantically, but there weren’t any dead moments—we talked the whole time. She did get mad that I’ve never seen The Notebook, though.”
Awkward Moment
Danielle: “His Instagram is private, and I mercilessly made fun of him. I was like, ‘How old are you? No one is going to see anything you post!’ I felt like a true millennial.”
Ben: “Before she got there, I was just sitting on the waterfront by myself. I started talking to everyone there, and I saw Alex Rodriguez walk in! I got a picture with him.”
Afterward
Danielle: “Embarrassingly, I hadn’t started a paper that was due, so I had to get home. He asked for my number and texted to make sure I got home safe, which was sweet.”
Ben: “I think she had homework, and being a gentleman, I didn’t want her to walk to the subway alone. I got her number on the train, gave her a hug, and then we parted ways.”
Verdict
Danielle: ♥♥♥♥ “He’s really genuine and outgoing. He was a good person to have my first grown-up date experience with. I think I want to hang out again—I’ll text him."
Ben: ♥♥♥♥ “I could see us being friends, but I don’t think she’s the future Mrs. Ben. Selena Gomez says the heart wants what it wants, and I didn’t get that feeling.”
Our daters went to La Marina (348 Dyckman St., 212-567-6300)
RECOMMENDED: Find more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.