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Meet the Undateables: Bri and Geoff

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:
Bri: She just moved to New York.
Geoff: He’s always looking for the next best thing.

Ideal date:
Bri: Anything that involves exploring the city
Geoff: Cocktails and then a comedy show


First impression
Bri: “I got there first and was sitting at the table enjoying the view, which was quite nice. When he arrived, he seemed super nice. He was really open and super easy to talk to.”
Geoff: “She probably wasn’t someone I’d necessarily pick for a first date. She wasn’t my typical type. She seemed a little standoffish and took a little time to warm up.”

Bri: “I didn’t feel any romantic chemistry, but he was really friendly. I don’t think either of us was nervous. Things were very easy between us. We had a great conversation.”
Geoff: “There wasn’t chemistry, and I think we were probably on the same page about that. I think she’d probably be more into someone who is more of an artsy, creative type.”

Awkward Moment
Bri: “There were all these people standing outside, and we found out there was a huge blackout. We ended up just walking to Bryant Park and talking there for another hour.”
Geoff: “She was into magic and spiritual things and the ethereal side of life. I’m not really sure if I believe in all that. She was very spiritual, and that was interesting.”

Bri: “I had to walk 20 blocks to take the tram back because of the blackout, so we said goodbye. He texted me so I’d have his number, gave me a hug, and that was it.”
Geoff: “We did exchange numbers. At this point, I don’t really know how I feel about it. It was very cordial. We were like ‘Let’s keep in touch’ but not sure if we would.”

Bri: ♥ “He was super friendly. I’m not sure if I’d see him again, but if I did, I think it would be in a friendly way. I definitely don’t think it can hurt, so we’ll see.”
Geoff:  “It wasn’t horrible. I just don’t think we’re compatible. It was a fun time, and we had an engaging conversation. It was great getting to know someone.”

Our daters went to Spyglass Rooftop Bar

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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