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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

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TK

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

THE DATE

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.”

Chemistry
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.”

Afterward
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.”

Verdict
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 undateable@timeout.com.

Best date ideas in NYC

Brooklyn Botanic Garden
Photograph: Shutterstock
Attractions, Parks and gardens

Brooklyn Botanic Garden

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.

Jane's Carousel
Photograph: Shutterstock
Attractions, Parks and gardens

Jane’s Carousel

Brooklyn Heights

As if Brooklyn Bridge Park weren’t already romantic enough with its staggering views of Manhattan and the bridges, this nearly 100-year-old hand-painted attraction will bring out the childlike glee in both of you. Keep the nostalgic feel going with a cone at the nearby Brooklyn Ice Cream Factory or get cultured with a sophisticated theater production at St. Ann’s Warehouse.

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Bars, Cocktail bars

Gallow Green

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) is this highly conceptualized romantic garden party meets cocktail lounge. During the warmer months, sit among the short trees and twinkling Christmas lights as actors from the downstairs play weave between the tables making charming conversation as socialite characters. Once winter hits, the space is given over to the Lodge, a meticulously crafted alpine cabin seemingly transported to the roof, complete with bunk bed and drawers filled with clues to the space. Grab a maple hot toddy and sit by the fire pit to revel in the full experience.

The Cliffs at LIC
Photograph: Courtesy Cliffs at LIC
Sports and fitness, Climbing

The Cliffs at LIC

Long Island City

If your date has been looking for adventure but ditching the city isn’t an option, take a couple of hours to harness that love of independence and thrills at this rock climbing facility. Take an introductory class together to learn the ropes (literally: how to tie them, how to belay and proper harness procedure) or let the staff hook you up and start scurrying up the tall walls. Competitive couples can try to beat each other’s times, and memberships are available should this become a favorite hobby for you and your partner in climb.

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Photograph: Francine Daveta
Nightlife, Nightlife

Slipper Room

Lower East Side

Drop your inhibitions at this seductive, throwback lounge—cheeky performers will leave you and your date laughing, curious and probably more than 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.

Shopping, Markets and fairs

Brooklyn Bazaar

Greenpoint

To do everything that the Brooklyn Bazaar offers all in one date will require a great deal of commitment, but if you and your love are up for the challenge, there’s great rewards in it for you. Goof off with mini golf and arcade games, sing your feelings at each other in the karaoke rooms, grab a fantastic dinner and drinks at Paradise Burger, and see an amazing performance or show in the concert venue.

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Nitehawk Cinema
Photograph: Gabi Porter
Movie theaters, Independent

Nitehawk Cinema

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. Already ate? The seasoned popcorn is far superior than the stale stuff you might find at other movie houses, while the full liquor and cocktail menu will make a boring, drawn-out flick more palatable.

Paulie Gee's
Photograph: Alex Strada
Restaurants, Pizza

Paulie Gee’s

Greenpoint

Though any date at this rustic Greenpoint pizza haven is likely to feel romantic with the dim lights and the delicious aroma wafting from the brick oven, up your game by traveling there on the East River Ferry. The short (and affordable) ride at sunset from Manhattan gives out-of-this-world views of the skyline surrounded by rich oranges and pinks that are almost as appetizing as the wine selection awaiting you just blocks away from the Greenpoint Ferry stop.

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Photograph: Shutterstock
Bars, Pubs

Literary Pub Crawl at White Horse Tavern

West Village

For those book lovers who get a kick out of the Hemingway quote “write drunk, edit sober,” take this long-running walking tour of the Greenwich Village. As you mosey your way through the historic nabe, an incredibly knowledgeable and friendly guide will point out the houses where literary powerhouses lived. And even better is the stops at long-running bars: Grab an ale and hear stories of inspired meetings, writing sessions and brawls that erupted when writers of yore took up residency in the drinking holes. Meets Fridays and Sundays at White Horse Tavern, 567 Hudson St (literarypubcrawl.com). $30. 

Chelsea Market
Photograph: Shutterstock
Shopping, Shopping centers

Chelsea Market

Chelsea

Rainy day blues, sweltering hot days and freezing cold nights don’t have to get in the way of your good time at the Chelsea Market. Mosey your way from sifting through vinyl records at Artists & Fleas, browse through the latest best sellers at Posman Books, toast regionally sourced oysters at the Lobster Place and chow down on homestyle cooking at Friedman’s.

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