Get us in your inbox

Photographs: Hollis Johnson

Meet the Undateables: Orlando and Renée

We're setting up New Yorkers who swear they’re totally undateable, and sending them out on socially distanced dates across the city

Will Gleason
Written by
Will Gleason

Why they’re single
Orlando: He has a hard time with trust.
Renée: She works too much.

Ideal date:
Orlando: Walking along the boardwalk on Coney Island
Renée: Meeting up for a cocktail


First impression
Orlando: "She was well put together and well dressed. Very polite. It looked like she was very open and into it. I would say she was definitely focused, open and intelligent.
Renée: "First impression was... I don’t know. I just kind of knew that that’s who he was. He was super easy to talk to. He was very personable, and he asked a lot of questions."

Photograph: Hollis Johnson

Orlando: "I did get the sense that we’re from different worlds, that’s for sure. We just come from different kinds of environments. But honestly, I think personality wise there was some compatibility. So that was kind of cool! We were able to talk pretty easily."
Renée: "There was no chemistry. We talked about work, family, pets, favorite movies, favorite books. We covered the whole gamut. Ninety minutes is a long time for a first date!"

Awkward Moment
Orlando: "Nothing super awkward. When I first got into the booth, I tripped a bit which was awkward. It also got a little quiet toward the end of the night. I was wondering if I should bring up something deeper, we were only talking about lighthearded things, but I decided to keep it lighthearted." 
Renée "There was a couple of awkward moments but the most was that there was a mix-up and he called me by the wrong name at the start of the date."

Photograph: Hollis Johnson

Dystopia Dating Vibes
Orlando: "We spent a lot of time talking about how we both avoid the subway and how things have been more dangerous in the street. Being outside in a booth when it’s cold is weird. Luckily, we had a heater which made it doable. Wearing a mask was weird. Honestly, this was the first date I’d been on since Covid. But it was about as weird as I thought it’d be."
Renée: "I was in full lockdown. I’ve only been out and about in small groups. But the restaurant did a really good job. They have these outdoor pods with heaters in them. For me, the most surreal thing was that I was out with someone I knew nothing about and I haven’t done anything like that since March. 

Orlando: "It’s funny. I took all the leftovers! She said she didn’t mind. I was kind of embarrassed about that, but I had to be real. She was cool about it. We walked to the corner. She got a cab, I was going to my car. We just said goodbye. I think we both knew we weren’t doing much more. It was cold that night, so I could tell she kind of wanted to get into the cab." 
Renée: "He drove. I was going to get a cab. We parked ways. We said it was nice to meet each other and then said goodbye! Just got out." 

Photograph: Hollis Johnson

Verdict [On a scale of five hearts]

Orlando:  "I would give it a three because there was a lot of compatibility, but we’re not gonna keep in touch or anything. Honestly, it was probably a little better than my expectations going in. I was imagining someone repulsive and she was much better than repulsive." 
Renée:  " it was an experience that I was glad that I did. I’m glad that I went but unfortunately it was not a love connection. He’s a very nice guy, though. We just weren’t a match."

Our daters went to e's BAR (511 Amsterdam Ave, Upper West Side)


Orlando: "The fries and the guacamole were really good. This is the first time I’ve ever had shishitos which I’d definitely recommend. The bar food was really good! The servers and staff were all nice and friendly. They had an outdoor area on the street and these plastic booths on the sidewalk with heaters in them."
Renée: "I had a burger and fries. The staff and the service was amazing. And their outdoor set-up for Covid is great. They have heaters, which is not super normal on the west side for some reason, and they were very well separated. The pods were nice, and the staff was great." 

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email

The 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
  • 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
  • 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. 

  • 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. 

  • 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. Just make sure it doesn’t turn into a kitchen competition — these classes contain knives!

  • 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 hideaway 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.

  • 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. 

  • Things to do

Stop and smell the roses (or the tulips) with your date at one of these incredible gardens inside NYC parks like Central Park or visit New York's various conservatories (like the one at the New York Botanical Garden), or at secret gardens in NYC that provide rare moments of solitude in a city packed with eight million people. Note that most of the stunning botanical gardens are requiring pre-reserved tickets at this time, so check their websites before heading out.

  • Things to do
  • Downtown Brooklyn

The seasonal 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
  • City Life

Coby Club is a subterranean lounge on Seventh Ave that’s inspired by 1960s San Francisco nightlife. The lush space 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.

    You may also like