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Meet the Undateables: Ann and Mike

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:
Ann: She’s been in school for a very long time and has forgotten how to interact with normal people.
Mike: He’s been burning the candle at both ends for years and didn’t have time for other things.

Ideal date:
Ann: Going to a bookstore and then getting some dessert
Mike: Going to a museum or park and then grabbing some cocktails


First impression
Ann: “I had no expectations, but I thought he was cute! He had an interesting shirt on that was light pink with tigers. He was friendly and easy to talk to.”
Mike: “My train got stuck underground, so I was almost late but made it just in time. She was really cute and also considerate, which put me at ease."

Ann: “We talked about a lot, from lighter topics to more serious things. He does improv and actually convinced me to take an intro class this week.”
Mike: “There was definitely chemistry. I can get kind of bored if I’m not intellectually stimulated in a conversation, but she really drew me in.”

Awkward Moment
Ann: “We both felt like it was weird to be on a blind date and both couldn’t stop bringing up how weird it was. But that kind of resolved the tension in a way.”
Mike: “We were sitting really close—our legs were kind of against each other—and I picked up my drink and then spilled it a bit. But luckily it was just on me."

Ann: “I was going to a show in Brooklyn and he lives there, so we decided to grab drinks in Fort Greene. We kissed at the bar a bit, and then a bit after.”
Mike: “After we left dinner, I could feel there was a connection. We were standing pretty close on the train, and there was a lot of touching and flirting.”

Ann: ♥ “He was funny and sweet and seemed to be able to talk about things in both a mature way and to have some fun about them.”
Mike: ♥ “It went pretty well. Honestly, I’ve been on a lot of dates recently, and this was a really good one. I would definitely want to go out with her again.”

Our daters went to A Summer Day Cafe (109 West Broadway, 646-882-0420)

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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