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Meet the Undateables: Harrison and Callie

Jillian Anthony

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:
Harrison: He recently got out of a four-and-half-year relationship.
Callie: She just hasn’t met the right guy yet.

Ideal date:
Harrison: An activity with both of us out of our comfort zone so we can experience it together
Callie: Grabbing drinks, then going to a sporting event or a show


First impression
Harrison: “I was waiting in line behind a girl. She was explaining to the front desk, ‘I’m meeting this guy Harrison.’ I said, ‘Um, hi.’ We hit it off right away; we had a lot in common.”
Callie: “He was a little shorter than [the guys] I usually date, and I also like men a little older. I didn’t feel like he was someone I’d go up to at a bar, but he was really nice.”

Harrison: “It was the venue’s first-birthday party in the rock climbing area; there were professional dancers and a DJ. We grabbed some drinks and chatted most of the night.”
Callie: “I wanted champagne, but they were only serving signature cocktails. I came back from the bathroom and Harrison had champagne for me—he convinced them.”

Awkward Moment
Harrison: “I told her that my family is really into Southwest Airlines, and she went on this whole rant about why she likes JetBlue. I was like, ‘All right, that’s cool.’ ”
Callie: “He talked about how great the date was going while we were in the middle of it. He was like, ‘Oh, this is going really well,’ and we’d only been there 20 minutes.”

Harrison: “I said I had a good time and she told me the same, then I asked for her number and walked her to her Uber. We’ve talked briefly over text, but it’s been a crazy week.”
Callie: “I had a holiday party to go. He asked to see me again and texted me after the date. He was very gentlemanly and said, ‘It was nice meeting you.’ ” 

Harrison: ♥♥♥ “She was a lot of fun, but I’m proceeding with caution. I can’t tell if she’ll be a good romantic partner or if there’s any chemistry until maybe a second date.”
Callie: ♥♥♥ “He was easy to talk to and really interesting, but I didn’t feel any type of sexual attraction. I enjoyed my time with him, but I wouldn’t pursue him.”

Our daters went to Brooklyn Boulders (718-482-7078,

RECOMMENDED: See more Undateables

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