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Photographs: Ann Sullivan

Meet the Undateables: Bobbie and Juan

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

Why they’re single:
Bobbie: She spends a lot of time with the wrong people.
Juan: He chooses to be, and he doesn’t want to waste people’s time.

Ideal date:
Bobbie: Going to a wine bar and then taking a long walk
Juan: A nice dinner and drinks


First impression
Bobbie: “I walked in and knew it was him pretty much immediately. He looked starkly like my ex-boyfriend, which freaked me out from the get-go. They even had the same glasses.”
Juan: “She had a very energetic vibe, which isn’t necessarily my type. I go for a bit more of a calmer energy. I’m really energetic and sometimes need a balance.”

Bobbie: “It didn’t feel romantic, but he was a really nice guy. He was just wearing a T-shirt and Yeezys, though. I was like, For a first date, you could step it up a little.
Juan: “I felt really comfortable, but I don’t think it was romantic. It felt more friendly. There was a lot of talk about life in general, but we didn’t really talk about past relationships.”

Awkward Moment
Bobbie: “There were a couple of awkward moments that kind of felt like, Oh, does he want to leave? I couldn’t really tell if he wanted to go. He also kept talking about being hungry.”
Juan: “I spilled a drink when I was walking because I didn’t know how to hold a martini glass. All of my drinks usually come in a cup.”

Bobbie: “We were there for about three hours, so we chatted for a long time. When we were leaving, we took the subway together and said goodbye. We didn’t exchange numbers.”
Juan: “There was a hug goodbye. We didn’t exchange numbers. But she actually knows someone who I perform improv with, so I was like, Hey, I’ll follow her on Instagram.”

Bobbie: ♥♥ “I had fun, but it was like I was catching up with a friend. I think part of it may be that he looked exactly like my ex. He almost felt kind of familiar.”
Juan: ♥♥ “I had a good time. I called my friend after, and I was like, ‘You should try Undateables!’ I had a great time getting to know her—she was a very nice person.”

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. 

  • Restaurants
  • Chinese
  • Midtown West
  • price 2 of 4

No one foresees anything good (with the possible exception of a Broadway show) to come out of Times Square. But consider Bugis Street Brasserie’s laksa: Comprising rice vermicelli, shrimp, chicken, fish cake and bean sprouts, this super-spicy noodle soup is sure to heat up your night. Your date might give you some side-eye as they’re guided into a hotel lobby packed with tourists, but sometimes great things emerge from unexpected places.

  • Things to do
  • City Life

Broke, huh? Well, it sounds like you’re craving a space so bucolic, you love birds will forget it’s free of charge! Everyone appreciates a hidden urban oasis, and the St. Luke in the Fields Gardens—just off Hudson Street, between Barrow and Christopher Streets in the West Village—are up there with the best of them.

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