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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

Will Gleason
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.

  • Things to do
  • Flatiron

The Museum of Sex always has something exciting going on behind closed doors. "Super Funland: Journey into the Erotic Carnival" is back and better than ever with its 4-D immersive “Tunnel of Love” ride, the Love & Lust Deity Derby game, an erotic fortune-telling machine (modeled as RuPaul), a kissing booth, the Glory Stall game, an immersive "Stardust Lane - the Erogenous Kaleidoscope," an erotic mechanical bull and a lit-up climbing structure, "The Climbx," and more. Then when it's time to take the edge off, visitors can slide down a spiral slide into the Museum’s psychedelic carnival bar, Lollipop Lounge, for cocktails. 

  • 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. 

  • Things to do
  • City Life

You don’t need to fly out west or cruise up to the Adirondacks to experience luxury camping. For a quick escape from the concrete jungle this fall, you can just head to a peaceful camping oasis on historic Governors Island. Collective Governors Island, the luxury campground on the western side of Governors Island, reopened last month and you can currently book a stay well beyond Labor Day Weekend.  The six-acre retreat, created by glamping hospitality group Collective Retreats, provides complimentary and unlimited access to a private water taxi from 4pm to 10pm daily for guests to arrive on the island and begin their getaways. 

  • Restaurants
  • Financial District

In a boomerang to its first location, Chikarashi Isso’s third form splits the difference between new restaurant and relaunch. Its lilting, 30-seat dining room is as lovely as ever, and fun tipples like Suntory whiskey highballs on tap will still be available, in addition to wine and sake. But Kobayashi’s menu is brand new. The chef’s selection of seasonal tempura, for example, might include shrimp, scallops and chrysanthemum, all recognizable even beneath a carefully-calibrated coating. Everything here, including the chicken karaage, dote beef stew and comfort food-adjacent hamkatsu, with turkey ham, gouda, herbs and tomato sauce, is meant to share...which is just another reaosn why it's perfect for a date.

  • Things to do
  • Games and hobbies

Get to know your date by performing a bank heist, a science experiment gone wrong or escaping from an ancient Egyptian tomb—that is, by solving an escape room! Since most escape rooms are blessedly climate controlled, these games are also an excellent thing to do on a rainy day. Take a look at best puzzle games and escape rooms in NYC below and get ready to put your wits to the test. 

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