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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.
Our daters had drinks and seafood at Pier A Harbor House (22 Battery Pl, 212-785-0153)
First impression
Joseph: “I got there a little early, so I thought every woman who walked by the table was her. It was a relief when Steph came. I thought she was pretty, and I liked her smile.”
Steph: “He looked bookish. He’s a writer, so it made sense. He was very attractive, just not my type. I like big schlubby Jewish comedians, and he was clean-cut.”
Chemistry
Joseph: “There were one or two moments when we paused, but I don’t think it was awkward. We had more than enough in common. I didn’t get the feeling she was turned off by me.”
Steph: “I’m super talkative, so I was directing the conversation. I don’t think he likes to talk a lot. If I didn’t speak, he might not have spoken. But he was very smart.”
Awkward Moment
Joseph: “I was starting to get sick, but I didn’t want to cancel, so I just popped a Tylenol, but I was definitely tired. When I felt it wearing off, I was like, Ugh, keep it together, Joseph.”
Steph: “He doesn’t drink, so I used both of our drink tickets. That’s when I knew we couldn’t have a future together. Mama likes a glass of wine with dinner!”
Afterward
Joseph: “I walked her to the subway and got her number. She only gave me her first name, so I asked my roommate if that was normal. I texted her later, and she wrote back.”
Steph: “He asked to exchange numbers, and there was a hug goodbye, no kiss. It was better than a handshake—it was an away hug. I was, like, angled behind.”
In three words
Joseph: Steph is "intelligent, funny and genuine."
Steph: Joseph is "smart, engaging and bookish."
Verdict
Joseph: ♥♥♥♥ “The date went really well. I’d like to go out again, but I don’t know if it would be romantic. Even if there isn’t another date, no regrets. I had a good time.”
Steph: ♥♥♥ “I would give it a solid B-minus. He was nice but quiet. We had a good time. We could definitely go have another drink, but it wouldn’t be romantic.”
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.