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Meet the Undateables: Jennifer and Brian

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:
Jennifer: She spent a lot of time in a relationship that wasn’t a good fit.
Brian: He hasn’t met the right one yet.

Ideal date:
Jennifer: Just grabbing a quick coffee or a drink
Brian: Drinks or coffee and then chilling in a park


First impression
Jennifer: “I noticed him when I arrived and hoped it was him. I was pleasantly surprised when it was. There was a moment of recognition, and it felt like the feeling was mutual.”
Brian: “When we first met, she said she really had to pee and I was like, ‘Please do that.’ So, I went and waited in line with her. We were chatting, and she seemed smart.”

Jennifer: “I think we had good chemistry from the get-go, and it only got better as the night went on. I was really excited that we had a lot to talk about. He seemed really great.”
Brian: “There weren’t really any awkward pauses or anything. We talked about a lot of things. Whatever came up, we were really able to run with it. We had a great night; it was fun.”

Awkward Moment
Jennifer: “When he went to pick up the second round of drinks from the bar, he was gone for so long that I was worried he had left—but then he came back, thank God.”
Brian: “When we were in the bathroom line, after I had just met her, the time came for her turn. She was like, ‘Do you want to come in with me?’ I was like, ‘Yes!’ Obviously, I didn’t.”

Jennifer: “I mentioned a concert at the Prospect Park Bandshell that night, and he was like, ‘Let’s go!’ So, we went there next and danced and kissed, and it was nice.”
Brian: “We danced, and the band was great. After that, I walked her home, and then I walked her dog with her. We exchanged numbers and have plans to go out again.”

Jennifer: ♥ “I was kind of shocked—it was great. We decided that we definitely wanted to see each other again before we left. We’re going out on a date next week.”
Brian: ♥ “I thought it might be a train wreck because I have a tendancy to be socially awkward, but it was great. I couldn’t believe how well it went. It felt very natural.”

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

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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