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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:
Avery: Always seems to get into relationships she knows won’t end well
Jared: Shows too much interest too early, and millennials don’t like that
Ideal date:
Avery: Going to a restaurant she’s never been to and sharing appetizers, then walking around the park eating shitty soft-serve
Jared: Spontaneous nonsense, like going to a thrift store and playing hide-and-seek
THE DATE
First impression
Avery: “He was already there, and he got up when I came to the table. He was a gentleman with a big smile on his face, and he had already built up a rapport with our server.”
Jared: “I was excited to see she was outgoing and witty, and I knew within 15 seconds that she was from the South, which I was kind of intrigued by.”
Chemistry
Avery: “I’m from Alabama, so he attempted a Southern accent—it was just fine for a New Yorker. We were comfortable with each other and silly from the get-go.”
Jared: “I thought with her being Southern, she might be a Trump supporter, so I brought that up to clear the air. She tried to trick me that she was, but I could see through that.”
Awkward Moment
Avery: “He named his college and literally after it came out of his mouth, this guy comes up and says, ‘Do you remember me from art class?’ I was sure he paid someone to do that.”
Jared: “When she came to the table, I tried to get up and hug her, but the waiter was in between us. So she sat down, and I felt like I should at least shake her hand or something.”
Afterward
Avery: “I had to be up really early, and we live in the same neighborhood, so we split a cab. He may have been going for a kiss good night, but I kissed him on the cheek.”
Jared: “We exchanged numbers in the cab. She texted me at 5am, because that’s when she woke up, which was likely difficult given the amount of alcohol we consumed.”
Verdict
Avery: ♥♥♥♥ “I had a really good time, but I don’t think he’s my type. If he planned a really fun date and said, ‘Hey, do you wanna do this?’ I’d say, ‘Yeah, sure, okay.’”
Jared: ♥♥♥♥ “I feel like we were mutually interested in each other on a romantic level. There was a lot of witty banter, which is how I like to interact with someone.”
Our daters went to Freud (506 LaGuardia Pl, 212-777-0327)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.