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Undateables Grace Anthony
Photograph: Young Skeletons

Meet the Undateables: Grace and Anthony

We take two New Yorkers who swear they’re totally undateable and put our matchmaking skills to the test.

Shaye Weaver
Written by
Shaye Weaver

Frustrated by the dating app struggle? We feel you. That’s why Time Out New York is relaunching the Undateables, a series in which we send two eligible singles on a date at some of our favorite NYC spots in the hopes of striking up a new spark. Following the night out, the daters report back with their candid thoughts on first impressions, chemistry and (of course) the inevitable awkward moments. This time, we sent Grace and Anthony to KYU, a wood-fired, pan-Asian barbecue restaurant in Noho—read on to see how it went. 

Interested in being set up on a blind date? Apply today by sending an email to

Undateables Grace Anthony
Photograph: Young Skeletons


Grace is a 28-year-old temp, babysitter and aspiring writer.

Anthony is a 29-year-old freelance writer.

Why they’re single: 

Grace: She’s picky because she wants genuine connection. She feels she’s “cynical” and “desperate” because of past bad relationships and longs for romance in a city “where dating has been replaced with ‘ethically non-monogamous’ relationships.”

Anthony: He’s a self-professed workaholic who hates leaving the apartment unless he needs to. He’s also “neurodiverse with a history of social anxiety” and lives in his head a lot as a playwright and producer.

Ideal date:

Grace: Drinks at a nice spot. 

Anthony: A show or a movie with drinks afterward and then home to smoke.


First impression:

Grace: “I got to the Jay Street/MetroTech subway stop and I was waiting for the train for almost an hour, so I freaked out and paid $50 for an Uber to get there from Downtown Brooklyn. He was very gracious about [me being 45 minutes late]. He was definitely very curious about me, which made things easier, but I could tell he was nervous.”

Anthony: “I thought she was very friendly and pretty. I felt bad because I was really anxious leading up to the date. We did hug each other, but I don’t know if I gave off a weird vibe.”

Undateables Anthony and Grace
Young Skeletons


Grace: “I didn’t necessarily feel any chemistry. He felt more like an acquaintance with friend vibes. We talked about movies, our backgrounds (we’re both Italian Americans), politics (we have the same values) so it was easy to talk and we had plenty to talk about.”

Anthony: “We talked about film and politics…and we were both pretty sure Michael Cohen was seated behind me. I had to keep my mouth shut. I am the most socially awkward person in the world. I’m autistic so it was hard for me. I had to practice discipline. It was creepy.”

Awkward moment: 

Grace: “Trump’s former lawyer Michael Cohen sat behind us.”

“I’m sure there were plenty of awkward moments but I can’t really say for sure—it’s me we’re talking about. She was very late. I didn’t want to be rude about it. I know trains sometimes get delayed. People work all sorts of hours and I didn’t know anything about her, but we got along.”


Grace: “We got on the same train line and we hugged ‘goodbye.” We followed each other on Instagram and he gave me his number, but I haven’t heard from him. We may talk again—it wouldn’t be out of the blue.”

Anthony: “It was friendly and ended well. If she contacts me, I wouldn’t be opposed to seeing her again, but I’m already back on the dating apps.”

Verdict [on a scale of five hearts]:

Grace: ♥ “He’s definitely someone you can tell is growing as a person.”

Anthony: “She is a good person and I do like her as a person, but I don’t think there was a ‘spark.’ I heard that Jon Stewart met his wife on a blind date and part of me was hopeful.”

The Date Spot:

Our daters went to KYU, a wood-fired, pan-Asian barbecue restaurant in Noho.

Grace: “I would recommend KYU as a date spot—the vibe was good and it was definitely causal but you could wear a nice dress if you wanted to.” 

Anthony: “The beef brisket was delicious, we had a s’mores cake and we had two good drinks. I’d recommend it if someone who has money wants to splurge. Maybe they’ll spot Rudy Giuliani. You never know.”

Maybelline Fit Me foundation was provided to Undateable participants along with concealer, powder and blush. Visit the Fit Me foundation match finder to find the perfect shade for you to wear on your next date.

Undateables Anthony and Grace
Photograph: Young Skeletons
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