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Photographs: Ann Sullivan

Meet the Undateables: Robert and Ceci

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test

Will Gleason
Written by
Will Gleason
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Why they’re single:
Robert: He just out of a long-term relationship and is working on his emotional availability.
Ceci: She recently got out of a relationship, so she’s new to the dating scene.

Ideal date:
Robert: Dinner at a diner, followed by an outdoor walk
Ceci: Bowling or going to a concert

THE DATE

First impression
Robert: “She was cute and friendly but dressed a bit casual, which made me think she wasn’t taking it too seriously. To be fair, I found out later that she was coming from work.”
Ceci: “He was super nice, and he was tall. He seemed a little shy at first, but then he opened up. He wasn’t the type I usually go for, but it was nice to kind of break out of that.”

Chemistry
Robert: “We had a flirty rapport. She was easy to talk to. We’re both newly single, so we compared notes on dating profiles, food, hobbies. The conversation flowed well.”
Ceci: “I’m not sure if it was romantic or friendly chemistry, but we ended up talking about a lot. I’m making a movie about mediocre first dates, and we laughed about that.”

Awkward Moment
Robert: “It wasn’t that awkward, but she has a shellfish allergy, and I really wanted to order some of the lobster dumplings. I ended up ordering them anyway.”
Ceci: “He asked me if I thought a photo of him was good, and I was like, ‘Honestly? Your eyes look a little weird.’ And he was like, ‘Oh, I’m actually kind of cross-eyed.’ ”

Afterward
Robert: “It was a beautiful night, so we got ice cream and walked along the water.  She had plans to meet a friend, so it was a quick date. We hugged, and I gave her my number.”
Ceci: “I had a friend that I had to meet, so I had to leave mid–ice cream. He asked for my number, and then we were like, ‘Let’s do this again.’ We’ve chatted a little since then.”

Verdict
Robert: ♥♥♥ “I’m not opposed to seeing her again, but I live in Astoria and she lives in East Williamsburg. Taking the N to the 7 to the G to the L seems rather daunting.”
Ceci: ♥♥ “He was a nice guy, and I enjoyed hanging out with him. Definitely chemistry, but maybe more friend chemistry. It went better than I expected!”

Our daters went to Time Out Market New York (55 Water St, 917-810-4855)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email undateable@timeout.com.

Best date ideas in NYC

  • Restaurants
  • Drinking

Taste great whiskey and learn some fascinating facts at Great Jones Distilling Co., which opened to the public in 2021 as Manhattan's first and only legal whiskey distillery in over 100 years. Over six years in the making, the 28,000 square-foot venue operates as a fully functioning distillery with a tasting room and several drinking and dining venues, including an underground speakeasy and a full restaurant. 

Couples can book several different experiences, including a tour detailing the whiskey-making process ($35), a culinary cocktail pairing experience ($145) and a hands-on mixology class ($110). 

  • Restaurants
  • Lower East Side

Ye’s Apothecary, which opened in June 2022 on the Lower East Side, quickly became New York City’s best new date place. Exceedingly pretty with has an air of speakeasy about it, the venue will turn "getting to know you" into a little more. Descend and make a sharp right: a cinematic bar is over your shoulder, set with gleaming emerald tiles and a few seats facing illuminated shelves as studied as a still life. The expanse of the long, jewel-toned venue is to the left, where elegant light fixtures float above banquettes and candlelit, marble tables.

It’s all very intimate, both as a euphemism for manageably tight and as a mood. 

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  • Sex and dating
  • Sex & Dating

How about a date that has been set up for you? The Metropolitan Museum of Art's beloved "Date Nights" give visitors an opportunity to become acquainted with artwork with informal drop-in gallery chats, the chance to listen in on gorgeous live music and sip on yummy cocktails.

"Date Nights" are held every Friday and Saturday nights in the American Wing Café from 5pm to 9pm. Even better, date nights come with museum admission, which is always pay-what-you-wish for New York State residents and NY, NJ, and CT students with valid ID. And this time, advance tickets are not required. 

The low-key dazzling Speakeasy Magick brings close-up magic table by table throughout a dark speakeasy where drinks flow and tricks await. 

Hosted by Todd Robbins (Play Dead), who specializes in mild carnival-sideshow shocks, Speakeasy Magick is a moveable feast of legerdemain. Audience members, seated at tables around McKittrick Hotel's Club Car speakeasy, are visited by a series of performers in turn.

Robbins describes this as “magic speed dating.” One might also think of it as tricking: an illusion of intimacy, a satisfying climax, and off they go into the night.

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  • Things to do
  • City Life

Board the Classic Harbor Line's for a romantic evening cruise on the '20s-style Yacht Manhattan—made extra cozy with ample pillows and corner tables—and order a glass of champagne. You'll pass the amazing One World Trade tower, sailboats gliding peacefully and Jersey City's many high rises. As the sun gets lower in the sky, the light bounces off different buildings, especially the Empire State Building, which seem to glow like a torch in the sky.

You can reserve your trip at classicharborline.com or call the Classic Harbor Line NYC phone number (212) 627-1825. Tickets cost $78 to $94 per person; make it a double date to get a price break on tickets.

  • Art
  • Art

Sure, those selfies on your phone are cute, but take things to the next level with professional selfies at the new FotoLab. It's NYC's first self portrait photography studio, and it makes for a super fun date. 

At this new Chelsea spot, you and your sweetie can cozy up in the studio to get some adorable photos together. There's music pumping through the studio, and you can bring some props (or a pet), so even if you're camera shy, you'll feel totally comfortable.

Maybe you'll even take things to a major next step and save this photo for a holiday card together.

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  • Restaurants
  • French
  • Greenwich Village
  • price 3 of 4

A West Village institution with classy decor, Minetta Tavern serves up that famous burger that’s on your bucket list. After your splurge, turn things up a notch at Marie’s Crisis Café, the iconic piano bar down the street. You can listen to some show tunes and join in the singing once you’ve got a few drinks in you. Who knows, maybe you and your date will harmonize!

  • Sports and fitness
  • Sports & Fitness

Go ahead and make a racket because ping pod pods—appropriately called PingPod—are now open across NYC. They're open 24/7, so whether you're looking for a daytime date or a late-night option, you can head to a PingPod location of your choice for some good old-fashioned fun. 

If your date can't volley some jokes while gently hitting a plastic ball across the table, well, maybe that's a foul.

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  • Nightlife
  • Nightlife
  • Lower East Side

Drop your inhibitions at this seductive, throwback lounge. Cheeky performers will leave you and your date laughing, curious and maybe a bit aroused. From your table by the stage (the space is small enough that there’s not really a bad seat in the house) expect the unexpected as aerial performers, singers, comedians, dancers and sexily clad lads and ladies perform circus and sideshow tricks. You’ll be hard-pressed to find anything like it in the Lower East Side—or anywhere else. Book tickets here.

  • Bars
  • Cocktail bars
  • Chelsea

Many of the city’s various rooftop bars rely heavily on their views as the main selling point for their overpriced drinks. But atop Chelsea’s McKittrick Hotel (the home of the famed Sleep No More) a highly conceptualized romantic garden party meets cocktail lounge.

The meticulously decorated Gallow Green rooftop switches up its style for each season, so there's always something new to discover. Just keep in mind that it's closed during the winter.

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