Can anyone explain why this date went wrong?

Dating

post #1

01-15-2016 at 05:16 am

Time Out New York, 1/2/2016

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:

Rui: Moved to  New York from Japan last spring, so hasn’t had a chance to meet new people and is still  learning English.
Jacob: His work  is pretty consuming and requires nights and weekends, but he’s working to make more time.

First impression

Rui: “He was wearing a suit, and he looked like a gentleman and a businessman. He’s nice, but it didn’t feel romantic. My type  is taller than me, and he was shorter.”
Jacob: “They sat her first and delivered me to  her, almost like a Bachelor episode. She was pretty and nicely dressed. She had a formal way about her but was very cordial.”

Chemistry

Rui: “We talked about our jobs, parents and where we’ve been. We found a mutual favorite restaurant in Astoria, but I didn’t  feel like I wanted to go there with him.”
Jacob: “This is her first year in America, so a lot  of the initial conversation was about what made her want to come to New York. But there was never a void in conversation.”

Awkward Moment
Rui: “His way of eating food is a little too messy. He spilled a lot of things on the table—dessert, bread, meat. It seemed he didn’t care about that, so I didn’t say anything.”
Jacob: “She asked when my last long-term relationship was and how long it lasted, which is a fairly forward thing to ask on a first date. I guess I was a little taken aback.”

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