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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.

  • 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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