Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right New York State icon-chevron-right New York icon-chevron-right Meet the Undateables: Harrison and Caralyn

Meet the Undateables: Harrison and Caralyn

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

Photographs: Ann Sullivan

Why they’re single:
Harrison: The apps are killing him.
Caralyn: She’s still just looking for the right person.

Ideal date:
Harrison: Getting a drink and some light appetizers and then talking a walk
Caralyn: Exploring a new neighborhood and finding a cool bar for a drink


First impression
Harrison: “My first impression was that she seemed very chill and down-to-earth. She was also really outgoing, which was refreshing. I would absolutely say that she was my type.”
Caralyn: “He wasn’t my usual type, but he was super nice. He broke the ice and was like, ‘This is a weird way to meet!’ He was a little bit shy. I did most of the talking.”

Harrison: “I think there was romantic chemistry. We talked about family, growing up—it turned out that we have a few friends in common. We both work in advertising, which was neat.”
Caralyn: “There wasn’t romantic chemistry. I thought he was cool and loved hanging out with him—I’m just not sure if there was that connection on my side. But never say never!”

Awkward Moment
Harrison: “The most awkward moment was definitely when I first met her. We both weren’t quite sure if we were the ones meeting each other, so we just stood there for a while.”
Caralyn: “Neither of us knew how to end it. We kind of skirted around how we would actually walk out. The most awkward part of the night was figuring out how to leave.”

Harrison: “We walked around the market, then said our goodbyes and exchanged numbers. I would like to see her in the future. I had a great time. I’m hoping we can do it again.”
Caralyn: “We exchanged numbers, he kissed me very briefly, and then we went our separate ways. He texted me to make sure I got home safe, which I thought was very nice.”

Harrison: ♥♥ “It went really well. I hope I have a chance to see her again. It was shockingly better than how I thought it might go. You never know with a blind date.”
Caralyn: ♥♥ “We had a lot in common. There just wasn’t a romantic spark. I kind of felt like I was spending the night hanging out with a friend. But he’s a great guy.”

Our daters went to Time Out Market New York (55 Water St, 917-810-4855)

RECOMMENDED: See more Undateables

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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.

Bars, Cocktail bars

Gallow Green


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.

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


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.

Nitehawk Cinema
Photograph: Gabi Porter
Movie theaters, Independent

Nitehawk Cinema


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


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.

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 ( $30. 

Chelsea Market
Photograph: Shutterstock
Shopping, Shopping centers

Chelsea Market


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.

Music, Cabaret and standards

Never Sleep Alone

Here's an idea for more, er, adventurous daters. Learn how to make love like a legend at this mesmerizing musical comedy/TED Talk hybrid, led by maverick author Dr. Alex Schiller (the alter ego of the brilliant Roslyn Hart). Through a series of hilarious and consent-affirming gauntlets, the good doctor will shake you out of romantic complacency. Live band performances of sexy songs will get you and your date feeling curious. And If you're not ready to face your fears of flirting onstage, be sure to select a "voyeur" ticket. But if you're ready to go big, the "participant" option will make you feel like you can breathe fire. Be sure to bring your A-game for a lit, highly-charged afterparty. For more information, visit

Things to do

The High Line

Though romantic walks are easily one of the most underrated cliché dates, few strolls are quite as magnificent as the High Line. At this park, a repurposed abandoned elevated railroad over 10th Avenue, you’ll see the Meatpacking District, Chelsea and the Hudson River at a whole new angle. As if the views of the bustling city beneath you weren’t enough, the plethora of gardens, sculptures and examples of amazing street art on the surrounding buildings are a sight to behold.

Coney Island Sand Castles 2015
Photograph: David Williams

Coney Island

Make like Patti Smith and the late Robert Mapplethorpe and plan an excursion to the ever-whimsical and wonderfully weird Coney Island. Explore the boardwalk, play some carnival games and scream your guts out on the Cyclone at Luna Park. Take cute selfies by the colorful Coney Island Art Walls, and for a bite, nosh on a Nathan’s Hot Dog.

Ace Bar
Photograph: Courtesy Stephen Kosloff
Bars, Dive bars

Ace Bar

East Village

You and your honey can have plenty of fun without spending much money at this East Village watering hole. Come during happy hour, which generously lasts until 8pm, for select $3 drafts as you unwind with games of skeeball, darts and pinball. There might be a bit of wait, but the pool tables are perfect for a friendly challenge—who ever wins buys the next round, or your cab ride to whoever’s apartment is closest.

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