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Meet the Undateables: Kyle and Ameed

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


Photograph: Ann Sullivan

Why they’re single:
Kyle: He’s looking for something stable and finds it hard to date in New York.
Ameed: He can be too direct, which can scare people off.

Ideal date:
Kyle: A flying-trapeze class followed by dinner with cocktails
Ameed: Walking around the park and then, if it goes well, grabbing a drink


First impression
Kyle: “There were instant smiles; I felt like maybe we had known each other before. He took his sunglasses off, and his eyes were really captivating. I would say he was my type.”
Ameed: “I was really nervous. Then I saw him, and he had a nice smile, so I thought we’d have a good time. We grabbed a drink and started talking. He seemed very open.”

Kyle: “There was romantic chemistry. He’s a creative type as well, so we were sharing our work with one another. I think we both kind of inspired each other, in a way.”
Ameed: “We talked about everything: where we’re from, what we’re doing. It went really smoothly. He was really engaging, which made it a lot easier.”

Awkward Moment
Kyle: “Before he got there, one of the [market ambassadors] and I really hit it off. She was really excited for me. Then she was like, ‘Can I actually take a selfie with you?’”
Ameed: “We got some tacos, and I tried to squeezed a lemon wedge over them, and then it kind of launched and went all over the place, which was awkward and embarrassing.”

Kyle: “After dinner, we went down and sat on the East River, exchanged a few kisses and then decided to walk the Brooklyn Bridge together before we parted ways.”
Ameed: “We walked the Brooklyn Bridge into the city. I didn’t get home until 11:30pm. It was perfect to walk over the bridge; it was quiet and really nice.”

Kyle: ♥ “I really do feel like we inspired each other. I think we both commented on how lucky we were that we were able to connect like that—almost like it was meant to be.”
Ameed: ♥ “We’re seeing each other again later this week for a second date. He was really creative and maybe not someone I’d match with on the apps, which was nice.”

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.

  • Things to do
  • Flatiron

The Museum of Sex always has something exciting going on behind closed doors. "Super Funland: Journey into the Erotic Carnival" is back and better than ever with its 4-D immersive “Tunnel of Love” ride, the Love & Lust Deity Derby game, an erotic fortune-telling machine (modeled as RuPaul), a kissing booth, the Glory Stall game, an immersive "Stardust Lane - the Erogenous Kaleidoscope," an erotic mechanical bull and a lit-up climbing structure, "The Climbx," and more. Then when it's time to take the edge off, visitors can slide down a spiral slide into the Museum’s psychedelic carnival bar, Lollipop Lounge, for cocktails. 

  • 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. 

  • Things to do
  • City Life

You don’t need to fly out west or cruise up to the Adirondacks to experience luxury camping. For a quick escape from the concrete jungle this fall, you can just head to a peaceful camping oasis on historic Governors Island. Collective Governors Island, the luxury campground on the western side of Governors Island, reopened last month and you can currently book a stay well beyond Labor Day Weekend.  The six-acre retreat, created by glamping hospitality group Collective Retreats, provides complimentary and unlimited access to a private water taxi from 4pm to 10pm daily for guests to arrive on the island and begin their getaways. 

  • Restaurants
  • Financial District

In a boomerang to its first location, Chikarashi Isso’s third form splits the difference between new restaurant and relaunch. Its lilting, 30-seat dining room is as lovely as ever, and fun tipples like Suntory whiskey highballs on tap will still be available, in addition to wine and sake. But Kobayashi’s menu is brand new. The chef’s selection of seasonal tempura, for example, might include shrimp, scallops and chrysanthemum, all recognizable even beneath a carefully-calibrated coating. Everything here, including the chicken karaage, dote beef stew and comfort food-adjacent hamkatsu, with turkey ham, gouda, herbs and tomato sauce, is meant to share...which is just another reaosn why it's perfect for a date.

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

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