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Meet the Undateables: Tim and Damien

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:
Damien: He's recently been focusing on his career.
Tim: He has a penchant for emotionally unavailable men.

Ideal date:
Damien: A stroll through Central Park, followed by a museum and drinks
Tim: Hitting up a bookstore or grabbing a drink


First impression
Damien: “I was very anxious, but that tension broke immediately when we started talking. He was easy to get along with, and it seemed like he had good morals and values.”
Tim: “I got there late and a little frazzled, but he was super nice and not at all pissed off. He was cute and charming and the only person I’ve dated who’s been taller than me.”

Damien: “We really dove into each other’s history and were sharing really deep stories. That made me feel a lot more comfortable, and I think he felt the same way.”
Tim: “The date lasted for three hours, and there was no subject  that was off limits, which is my ideal date. He seemed as interested in getting to know me as I was in him.”

Awkward Moment
Damien: “The food was great, but the restaurant had a cheese-heavy menu, and I’m lactose intolerant. I took a few Lactaids before and just woke up lethargic the next day.”
Tim: “The cheese came out, and he was like, ‘Oh, I’m lactose intolerant,’ and I laughed. But he was like, ‘Oh, no, really! I’m really lactose intolerant.’ He took some Lactaid.”

Damien: “We had dessert and then headed out and walked to the subway. We exchanged numbers and planned for a second date. I definitely think I’ll see him again.”
Tim: “He walked me all the way to my subway stop, even though it was three avenues away. There may have been a smooch or two. I think we’re gonna go on another date.”

Damien: ♥ “I was pleasantly surprised. This was my first blind date, and it was a lot of fun. The anticipation was nerve-racking, but it ended up working out okay for me.”
Tim:  “He seemed like a genuinely sweet, nice guy. He blew it out of the water with how much better it was than what I was expecting. It was just really easy.”

Our daters went to Raclette (511 East 12th St917-853-5377)

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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