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Meet the Undateables: John and Danielle

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


Photograph: Ann Sullivan

Why they’re single:
John: He broke up with his longtime girlfriend in January.
Danielle: She gets ghosted a lot and finds it hard to make a connection online.

Ideal date:
John: Taking a cooking class at the International Culinary Center
Danielle: A live show or podcast recording, followed by a drink at a low-key bar


First impression
John: “I got there early. I was nervous and wanted to make sure everything was lined up. When she came in, she looked great—very manicured, beautiful and clean-cut.”
Danielle: “The hostess said they seated him at the bar. There were two guys there, and I was like, Oh, thank God it wasn’t the other one. He was really cute and very personable.”

John: “At first, she was a little too quiet. After the first hour, she opened up a bit more, and her personality really meshed with mine. We ended up talking for five hours.”
Danielle: “I think there was an initial attraction, and then, just personality-wise, we got along really well. I think we were on the same page about a lot of things.”

Awkward Moment
John: “She was eating a soup dumpling, and it squirted all over the place. We just giggled about it, and then I did the same thing, so she didn’t feel too awkward about it.”
Danielle: “I was teasing him about cutting into his soup dumpling on the plate and letting the broth pour out. Then I bit into mine and the broth just went everywhere.”

John: “We kept talking over dessert and had a couple more rounds of drinks. I took her to the subway stop, we kissed and exchanged numbers, and then I went home.”
Danielle: “We left and exchanged numbers outside. Based on the state of my glasses after, there was some making out, but I don’t really remember. I was pretty drunk.”

John: ♥ “We’ll see each other again. I haven’t had many five-hour experiences like that with another human being. It was fun and easy in the most flattering way.”
Danielle: ♥ “It was the best first date that I’ve had in a long time. It went great. I was sort of worried about it, but it ended up being a lot better than my expectations.”

Our daters went to Brooklyn Chop House (150 Nassau St, 212-619-1200)

RECOMMENDED: See more Undateables

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

Best date ideas in NYC

  • 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!

  • 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 laddies perform circus and sideshow tricks. You’ll be hard-pressed to find anything like it in the Lower East Side—or anywhere else.

  • Things to do
  • Downtown Brooklyn

Dreamland Roller Disco in Prospect Park provides a modern twist on a retro date. Besides, isn’t there something cute about falling on your butts together? What makes Dreamland special are its themed nights. From Gaga vs Madonna to Soul Train to Y2K Disco, you're bound to find the perfect theme that will get you going regardless of your skating skills.

  • Restaurants
  • Austrian
  • Ridgewood

The Austrian-inspired cuisine and lived-in but chic aesthetic make Porcelain a charming first-date option. The prices are refreshingly low, too, with plates in the $10 range. Grab a couple of big, plush chairs, then split brunch and a pastry or three. If that’s not as sweet as can be, we don’t know what is. 

  • Attractions
  • Arcades and amusements
  • Midtown East

New York is brimming with unique, exciting activities. But if you’re pining for something truly cutting-edge, explore another city—or another planet, for that matter—by bringing your date to VR World, a theme park that proffers 50 mind-bending interactive experiences.

  • Restaurants
  • Italian
  • Brooklyn Heights

Versatility is a key quality in a date spot: somewhere you want to stay but can still bolt if need be. If that’s what you’re seeking, get thee to Jared Braithwaite’s bar Pips, which sports an impressive wine selection alongside small plates inspired by coastal Italian cuisine. Plus, it’s right on Atlantic Avenue, so your subway escape-route options are plentiful. 

  • Attractions
  • Parks and gardens
  • Prospect Park

You and your special someone don’t have to travel far to feel like you’re in an idyllic pastoral paradise with this century-old Kings County NYC park. Nestled away by Prospect Park, you’ll find over 50 acres of cherry blossoms, rose gardens and the bright flora of the tropics in the balmy conservatory. No matter the season, you’ll be sure to see beautiful plant life.

  • Movie theaters
  • Independent
  • Williamsburg

Why bother going to two separate places when you can combine this classic date at one fantastic eat-in cinema? Grab one of the luxurious, big comfy chairs and take advantage of the table with the seats. Chow down on tacos, burgers, charcuterie or small plates as you take in buzzworthy indie films and retro re-releases. And be sure to take advantage of the sweet cocktail and beer menu. 

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