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Photograph: Ann Sullivan

Meet the Undateables: Alexis and Nicole

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

Why they’re single:
Nicole: She's focused on her career, so she really doesn't have time to date.
Alexis: He's working on himself right now and isn't really looking for a specific person.

Ideal date:
Nicole: Bowling or going to a beer hall
Alexis: Going to a music concert


First impression
Nicole: “I could tell it was him right away because he seemed really anxious. He was kind of pacing back and forth. He seemed very shy and nervous and wasn't really my type."
Alexis: “I wasn't nervous at all. I'm not a nervous guy. My first impression of her was that she seemed really laid-back. I felt pretty comfortable with her. She was really talkative." 

Nicole: “There was a little-brother vibe. We talked about our ethnicities and how it can be hard to deal with. Dealing with racism is kind of an uncomfortable first-date topic”
Alexis: “No romantic chemistry. It was more like a friend meetup than a romantic one. We talked about work, the areas we live in, the places we're from—we talked a lot.”

Awkward Moment
Nicole: “I asked if he wanted any of my fries, and then he just ate all my fries—like, he took big handfuls of fries from my plate. He really went to town on my fries."
Alexis: “I was eating her fries the whole time we were talking. I'm not sure if she liked that. It was kind of awkward when I looked down and there were no more fries."

Nicole: “I had a work party to go to, so from the get-go I told him I had to ditch early. He stayed in the market, and I left. We exchanged Instagrams but not numbers."
Alexis: “She had to go to a coworker's party. I asked for her Instagram, and I followed her. I don't know if I'll see her again because she didn't follow me back."

Nicole:  “I went fine. I just felt like I was hanging out with my little brother. I didn't really feel like we were right for each other. We were in two different life stages."
Alexis: ♥♥♥ “She was really nice, but it just felt kind of friendly. She wasn't really my type, but I definitely felt like we could become friends."

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
  • Drinking

Taste great whiskey and learn some fascinating facts at Great Jones Distilling Co., which opened to the public in 2021 as Manhattan's first and only legal whiskey distillery in over 100 years. Over six years in the making, the 28,000 square-foot venue operates as a fully functioning distillery with a tasting room and several drinking and dining venues, including an underground speakeasy and a full restaurant. 

Couples can book several different experiences, including a tour detailing the whiskey-making process ($35), a culinary cocktail pairing experience ($145) and a hands-on mixology class ($110). 

  • Restaurants
  • Lower East Side

Ye’s Apothecary, which opened in June 2022 on the Lower East Side, quickly became New York City’s best new date place. Exceedingly pretty with has an air of speakeasy about it, the venue will turn "getting to know you" into a little more. Descend and make a sharp right: a cinematic bar is over your shoulder, set with gleaming emerald tiles and a few seats facing illuminated shelves as studied as a still life. The expanse of the long, jewel-toned venue is to the left, where elegant light fixtures float above banquettes and candlelit, marble tables.

It’s all very intimate, both as a euphemism for manageably tight and as a mood. 

  • Sex and dating
  • Sex & Dating

How about a date that has been set up for you? The Metropolitan Museum of Art's beloved "Date Nights" give visitors an opportunity to become acquainted with artwork with informal drop-in gallery chats, the chance to listen in on gorgeous live music and sip on yummy cocktails.

"Date Nights" are held every Friday and Saturday nights in the American Wing Café from 5pm to 9pm. Even better, date nights come with museum admission, which is always pay-what-you-wish for New York State residents and NY, NJ, and CT students with valid ID. And this time, advance tickets are not required. 

The low-key dazzling Speakeasy Magick brings close-up magic table by table throughout a dark speakeasy where drinks flow and tricks await. 

Hosted by Todd Robbins (Play Dead), who specializes in mild carnival-sideshow shocks, Speakeasy Magick is a moveable feast of legerdemain. Audience members, seated at tables around McKittrick Hotel's Club Car speakeasy, are visited by a series of performers in turn.

Robbins describes this as “magic speed dating.” One might also think of it as tricking: an illusion of intimacy, a satisfying climax, and off they go into the night.

  • Things to do
  • City Life

Board the Classic Harbor Line's for a romantic evening cruise on the '20s-style Yacht Manhattan—made extra cozy with ample pillows and corner tables—and order a glass of champagne. You'll pass the amazing One World Trade tower, sailboats gliding peacefully and Jersey City's many high rises. As the sun gets lower in the sky, the light bounces off different buildings, especially the Empire State Building, which seem to glow like a torch in the sky.

You can reserve your trip at or call the Classic Harbor Line NYC phone number (212) 627-1825. Tickets cost $78 to $94 per person; make it a double date to get a price break on tickets.

  • Art
  • Art

Sure, those selfies on your phone are cute, but take things to the next level with professional selfies at the new FotoLab. It's NYC's first self portrait photography studio, and it makes for a super fun date. 

At this new Chelsea spot, you and your sweetie can cozy up in the studio to get some adorable photos together. There's music pumping through the studio, and you can bring some props (or a pet), so even if you're camera shy, you'll feel totally comfortable.

Maybe you'll even take things to a major next step and save this photo for a holiday card together.

  • 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!

  • Sports and fitness
  • Sports & Fitness

Go ahead and make a racket because ping pod pods—appropriately called PingPod—are now open across NYC. They're open 24/7, so whether you're looking for a daytime date or a late-night option, you can head to a PingPod location of your choice for some good old-fashioned fun. 

If your date can't volley some jokes while gently hitting a plastic ball across the table, well, maybe that's a foul.

  • 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 ladies perform circus and sideshow tricks. You’ll be hard-pressed to find anything like it in the Lower East Side—or anywhere else. Book tickets here.

  • Bars
  • Cocktail bars
  • 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) a highly conceptualized romantic garden party meets cocktail lounge.

The meticulously decorated Gallow Green rooftop switches up its style for each season, so there's always something new to discover. Just keep in mind that it's closed during the winter.

  • 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 you can easily catch a subway home if you're just not that into your date. 

  • Things to do

Be like Danny and Sandy in Grease and go to the drive-in. Though these movie theaters in NYC may seem to belong to a different era, this nostalgic entertainment form has made its way back into the spotlight.

For your next date night, order takeout from your favorite restaurant, pack a picnic full of snacks, and enjoy a flick at one of these drive-in theater locations in and around the concrete jungle.

  • Attractions
  • Parks and gardens

The New York Botanical Garden is one of the best New York attractions for a reason—it has a 50-acre forest, a palace modeled after Spain’s Alhambra, a rose garden, an observatory and plenty of spots to hide away from it all. Plus, it hosts plenty of beloved events like winter's Holiday Train Show and the Orchid Show. During the fall, its collection of pumpkins is epic. This kind of date is for those who want to escape from the city without actually leaving.

  • Art
  • Contemporary art

New York City is full of free outdoor art that you don't even have to go to a museum to see. Sculptures, murals and photographs can be found in its parks, sidewalks and on its buildings!

Locations such as the High Line, Central Park, the Metropolitan Museum Of Art, Cadman Plaza in Brooklyn, Socrates Sculpture Park in Queens and other NYC locales all have a wide variety of pieces awaiting you, from massive sculptures to eye-popping murals and graffiti.

We've got a list of more than a dozen outdoor artworks to go see, making for a date that costs nothing but means a lot.

  • Movie theaters
  • Independent
  • Williamsburg

Why bother going to two separate places when you can combine this classic date at one fantastic eat-in cinema at Nitehawk? 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. 

  • 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 our list of the best puzzle games and escape rooms in NYC and get ready to put your wits to the test. 

  • Things to do
  • Classes and workshops

From basic culinary skills to cooking with wine to rolling sushi, these couples cooking classes aim to entertain and educate. You’re sure to grow closer as you mix ingredients with your special someone. As the oven heats up, so too will your love. 

  • Things to do
  • City Life

A subterranean lounge on Seventh Ave that’s inspired by 1960s San Francisco nightlife, Coby Club's lush space makes for a glam evening. The venue pays homage to San Francisco Chinatown nightlife in the 1960s and one woman in particular who was at the heart of it: Miss Coby Yee, the glamorous dancer and owner of the iconic club Forbidden City. With black velvet banquettes and red, silk-shaded lighting, this is the spot to kindle romance.

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