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Meet the Undateables: Lisa and Demar

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:
Lisa: She doesn’t prioritize dating.
Demar: He’s looking for a genuine connection but just hasn’t met the right person.

Ideal date:
Lisa: Dinner and a good comedy show
Demar: Dinner and drinks


First impression
Lisa: “I thought he was really handsome, but I was taller than him in heels, which I didn’t care for. He was really intelligent and engaging. He seemed very smart.”
Demar: “I got there late and a little frazzled, but he was super nice and not at all pissed off. He was cute and charming and the only person I’ve dated who’s been taller than me.”

Lisa: “I felt like he acted a bit younger than his age. He was mature about a lot of things, but, just socially, he seemed like he was in a bit of a younger stage in his life.”
Demar: “I got more of a friends vibe. She was very inquisitive. She asked a lot of good follow-up questions. If there had been an attraction, it would have been a great first date.”

Awkward Moment
Lisa: “I asked him what he thought was the appropriate time to say ‘I love you’ to someone, and he said a month and a half. I was like, Woah, buddy. I’d say closer to six months.”
Demar: “I yawned a couple of times toward the end of the night, and she was like: ‘You’re the first person to ever yawn on a date with me.’ I wasn’t bored—it was just getting late.”

Lisa: “He asked me if I would go on a second date with someone if he was, like, a six out of 10. I couldn’t tell if he was asking about us or just in general. I said no.”
Demar: “We hugged goodbye and then both got cabs. We didn’t exchange numbers, and I don’t think I’ll see her again. The night kind of felt like talking to an old friend.”

Lisa: ♥ "I had no expectations about how it might go, and it went fine. It turned out to be pretty okay. It could have been worse. It just didn’t quite feel romantic.”
Demar: ♥ “The night wasn’t awkward in any sense. The food was good; the restaurant was great. I kind of want to go back to hang out with the bartender.”

Our daters went to Gupshup (115 East 18th St, 212-518-7313)

RECOMMENDED: See more Undateables

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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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