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Meet The Undateables: Samantha and Tim

Will Gleason
Written by
Will Gleason

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:
Samantha: She enjoys being single, and a lot of the guys she likes are emotionally unavailable.
Tim: He works all the time and doesn’t get out enough to meet people.

Ideal date:
Samantha: Something competitive like bowling and then checking out a unique bar
Tim: Meeting at a bar or a restaurant and then maybe a walk in a park


First impression
Samantha: “He was smiley right from the start. I was excited as well, and I always like to mirror someone’s personality because I think that makes things more enjoyable.”
“I was like, ‘Holy shit! This person definitely has her shit together.’ I was feeling out of my league. Not in the usual way but, like, in how put together she was.”

Samantha: “We got along well but more in a platonic sense than anything romantic. I didn’t feel a spark. I usually get that within 30 minutes of talking to someone.”
“We really hit it off. I didn’t push much because I could tell she wasn’t pushing for more. Usually on a date, you feel like doing more, but I wasn’t sure in this scenario.”

Awkward Moment
Samantha: “I couldn’t tell his age initially, but he told me and I was like, ‘Oh. That makes a lot of sense.’ I tend to usually date guys much older than myself.”
“I said I was too young to see Jurassic Park [when it came out], and she asked my age. That doesn’t matter to me, but it sounds like it did to her.”

Samantha: “As we were leaving, he talked with the staff about shooting there. It portrayed that he’s always ready to work, even if he doesn’t have standard employment.”
“I looked at the time, and we decided to head out. I went in for a handshake and she went for a hug. I got her number to be friendly. She was very nice. Very, very cool.”

Samantha: ♥♥♥ “It was a really enjoyable evening. I left feeling like I made a good friend who I could contact for doing something spontaneous. But emphasis on the friend.
Tim: ♥♥♥ “It was great. She was really friendly, really professional. There wasn’t a mean bone in her body. We had a fun time, but I didn’t feel that romantic energy.”

Our daters went to Esther & Carol (341 Broome St, 646-355-1840)

RECOMMENDED: See more Undateables

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