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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
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.

  • 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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