Photograph: Ann Sullivan
Why they’re still single:
Sarah: She’s really busy and enjoys the single life.
James: With his schedule, he’s usually only free late at night.
What they learned from their last Undateables date:
Sarah: If you go in with zero expectations, you’ll feel a lot less nervous.
James: It’s easier to talk to someone who is following their passion.
Sarah: “I thought he was really nervous and kind of shy. He stumbled over his words a lot. He was really sweet, but it just took a while for him to get into the conversation.”
James: “She was nice, but I didn’t have much to talk about with her. Once she knew I worked in the theater, she only wanted to talk about famous people I’ve worked with.”
Sarah: “I wouldn’t say there was much chemistry—it was a pretty basic conversation. We talked a lot about things to do around the city. He grew up here and had great recs.”
James: “I couldn’t get a read on her, so it was hard for me to tell what she was looking for. Also, she didn’t know where Flushing was, even though she’s been to a Mets game.”
Sarah: “We were at a cocktail bar with 25 different, really cool cocktails on the menu, and he ordered a rum and coke. I gave him a hard time about it, but I was just kidding.”
James: “She kept apologizing for liking basic things, and I was like, ‘I don’t care if you like Taylor Swift or Ariana Grande! That’s fine! Why are you apologizing to me? I’m just a man you met in a bar.’ ”
Sarah “He asked if I wanted to do this again sometime, and I said I wasn’t really sure. He was going to take the same subway as me, but then he said he was just going to walk.”
James: “To be polite, I asked her if she wanted to go out again. She said no but then said she’s never been asked out on a second date before. I thought that was strange.”
Sarah: ♥♥♥ “He was really sweet, a total gentleman. As a date, it was great, but there wasn’t really any chemistry. From the last date to this one, we’re moving in the right direction.”
James: ♥♥ “I’ve had better dates. I would go back to that bar with someone who I really liked, though. Actually, there’s someone else I really like that I might take there.”
Our daters went to The Up & Up (116 Macdougal St, 212-260-3000)
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