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Meet the Undateables: Scott and Randi

Written by
Dana Varinsky

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:
Scott: Has been traveling a lot since college 
and is just now starting to 
feel ready to settle down
Randi: Finds it hard 
to meet people organically 
in the city, and online dating 
has a hookup vibe

Ideal date:
Scott: An art gallery, 
gelato and a walk on 
the High Line
Randi: Drinks at 
a speakeasy or cocktail bar


First impression
Scott: “She looked professional, confident and secure, which is positive, but my type is an artist having an existential crisis. I’m a sucker for someone confused and wandering.”
Randi: “He’s not my normal type—he had long hair and was kind of skinny and a little shorter than me. I usually go for taller guys with shorter hair, but he was really nice.”

Scott: “It was actually an impressive match. We’re both liberal, Jewish and digital advertisers. The attraction wasn’t there, but it was super fun.”
Randi: “We talked for two hours nonstop. I was pleasantly surprised at how well we got along—we had so much in common. 
I laughed a lot. He was really sweet.”

Awkward Moment
Scott: “When we went up to the host, I wasn’t 
sure what to say, so I was like, ‘Um, I’m undateable?’ The host just gave me that one-eyebrow-raised look.”
Randi: “The girls next to us were very drunk and singing Third Eye Blind. We’d wondered if it was a birthday or bachelorette, and then they brought out a dessert with a sparkler.”

Scott: “We walked to where she could hail a cab. 
I gave her a hug and said, ‘Let’s keep in touch.’ I wouldn’t be interested in dating, but it would be a blast to be friends.”
Randi: “We got dessert, and then we walked out, hugged and exchanged numbers. He texted me after, and I responded. He was like, ‘Oh, good, not a fake number!’”

Scott: ♥♥♥♥ “We had a lot in common. She’s supercool but unfortunately not the type 
I’m looking for. I’m sincerely interested in meeting up as friends in the future, though.”
Randi: ♥♥♥♥ “Going in not knowing more than someone’s first name is kind of terrifying, but I had a really good time. He’s a great guy. I’d definitely go out again.”

Our daters went to Cantina Rooftop (605 W 48th St, 212-957-1700)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email

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