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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

By Will Gleason
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TK

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

THE DATE

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."

Chemistry
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."

Afterward
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.”

Verdict
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 undateable@timeout.com.

Best date ideas in NYC

Marie's Crisis
Photograph: Time Out/Ali Garber

Feast at Minetta Tavern, then drink and sing at Marie’s Crisis Café

Restaurants French Greenwich Village

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!

Photograph: Francine Daveta

See a burlesque show at the Slipper Room

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.

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Dreamland Roller Disco
Photograph: Courtesy Dreamland Roller Disco

Couple skate during Dreamland Roller Disco

Things to do Downtown Brooklyn

Dreamland Roller Disco 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. February is chock-full of romantic rendezvous, such as the upcoming disco party I Feel Love on Valentine’s Day. 

City Point BKLYN, Downton Brooklyn (dreamlandrollerrink.com). $20–$26 (includes skate rental).

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Porcelain
Photograph: Time Out/Ali Garber

Get cozy on the cheap at Porcelain

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. 

Kick Axe Throwing
Photograph: Courtesy Kick Axe Throwing

Sharpen your skills at Kick Axe Throwing

News Drinking

Craving an out-of-the-ordinary daytime date that doesn’t involve drinking the afternoon away? Kick Axe Throwing, in Gowanus is an urban adventure that's bound to make you look like a badass—plus, it opens at 11am during the week. Before chucking those hatchets, peruse the Runner & Stone café a few blocks away for a caffeine or pastry fix.

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Photograph: Courtesy VR World

Trip out at VR World NYC

Attractions Arcades and amusements Midtown

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.

Photograph: Courtesy Pips / Liz Clayman

Stay for a while (or just a minute) at Pips

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. 

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Brooklyn Botanic Garden
Photograph: Shutterstock

Bask in the beauty of the Brooklyn Botanic Garden

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.

Nitehawk Cinema
Photograph: Gabi Porter

Feast and catch a flick at Nitehawk Cinema

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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