Get us in your inbox


Lauren and Tyler

We sent two past Undateables out on a brand-new blind date to give them a second shot at love.

Will Gleason
Written by
Will Gleason


Photograph: Ann Sullivan

Why they’re still single:
Lauren: She still hasn’t come across the right guy.
Tyler: He’s busy as hell at work.

What they learned from their last Undateables date:
Lauren: When on an iffy date, you should trust your gut reaction.
Tyler: It can be great going into a date with absolutely no expectations.


First impression
Lauren: “He showed up a little late, and he seemed a little frenzied because he just came from work. He was really apologetic. I got good vibes from him right away.”
Tyler: “I was about 15 minutes late, as per usual, but it was a great first impression. It was good to meet someone with a smiling face. She was easy to talk to from the get-go.”

Lauren: “I’ve never dated a guy with long hair before, so that was new. But other than that, definitely my type. He was very personable, charismatic and a great conversationalist.”
“Personality-wise, I think we got along pretty well. We didn’t have any dull moments. Right off the bat, we made some corny jokes that didn’t land, but we kind of eased into it.”

Awkward Moment
Lauren: “When I first got to the bar, they led me toward the back. There was this guy there, so I went in for a hug with him. Then he was like, ‘No, not me—I’m the manager.’ ”
Tyler: “She told me her first [Undateables] date kept talking about his health problems. I was like, ‘Well, I have celiac disease, so I guess that’s a trend in your life!’ ”

Lauren: “Tyler had to run back to work but said we should definitely hang out again and asked for my number. So we hugged goodbye outside the bar and parted ways.”
Tyler: “We were there for over three hours, so we decided to head out. I got her phone number. It ended a little abruptly, but I think we could potentially see each other again.”

Lauren: ♥ “Much better than my last date. He seemed like the kind of person who would make any situation more fun. I would be interested to get to know him better. Two thumbs up!”
Tyler: ♥♥♥♥ “There wasn’t a romantic spark, but we had a great conversation. You know things are good if you can talk politics and don’t feel like ripping each other’s heads off.”

Our daters went to Stay Gold (360 Third Ave, 917-261-7441)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email

Looking for a cheap date idea?

Graphic Love Stories
Photograph: Courtesy Desert Island

Graphic Love Stories

Nerd is the new cool and nothing says nerdtastic like a good comic book. Geeky sweethearts, make your way to Williamsburg's quaint comic book store, Desert IslandDiscover each other's favorites or grab a copy of Smoke Signal, the shop's free weekly anthology.

Sets you back: FREE

Free gigs and high-end cocktails

Free gigs and high-end cocktails

Wait until you’ve been out a few times and you’re ready to squeeze in nice and close before hitting the teeny back room of Pete’s Candy Store, which hosts no-cover shows by indie artists and acoustic troubadours every night of the week. Afterward, head around the corner to The Shanty, a naked brick-and-concrete bar attached to the New York Distilling Company that offers some pretty sweet happy hour specials.

Sets you back: $16–$24

  • Bars
  • Pubs
  • Park Slope

No matter how tight your budget, you can still get loose on the dance floor at Park Slope's Union Hall. Free dance parties go down most Saturday nights, featuring DJs spinning old-school hip-hop crowd pleasers and heavy-hitters at midnight. Check out the drink specials and definitely split a basket of fries ($6) or an order of deviled eggs ($5)—served until midnight —before you hit the dance floor.

Sets you back: $18

Dessert and nerdery
Photograph: Lizz Kuehl

Dessert and nerdery

It’s been scientifically proven that nothing in the known universe is more romantic than pie. At Gowanus go-to Four & Twenty Blackbirds, two slices of shop faves like salted apple caramel or grapefruit custard will run you $11.50. (Arrive early in the evening, as they tend to sell out.) Then, fill your head with, you know, actual scientifically proven knowledge at the Bell House at a trivia night or Secret Science Club. Tip: Bring someone geeky to this, lest you seem…like a total geek.

Sets you back: $11.50

Nature and history in the Bronx
Photograph: Francis Smith

Nature and history in the Bronx

Seeing an outdoorsy guy or gal but don’t have the gas money to drive upstate? Fortunately, there’s ample natural beauty to explore in Van Cortlandt Park. The secluded banks of Van Cortlandt Lake (in the southwest region) are begging for a quiet but passionate make-out session. Post-smooching, stop by the Van Cortlandt House Museum ($5), just west of the lake. Its 1740s stone edifice hosted George Washington twice in the midst of the Revolutionary War, and the current interior features re-creations of furnishings favored by the abode’s namesake, the rich merchant and mayor Jacobus Van Cortlandt.

Sets you back: $10

A cinematic shrine and plenty of Guinness
Photograph: Jessica Lin

A cinematic shrine and plenty of Guinness

Secure film-buff status by bringing your date to the Museum of the Moving Image on Thursday from 2-6, when the admission fee is waived. Make sure to fool around at the permanent collection’s sound-editing, dubbing and stop-motion-animation stations before leaving. Afterward, drink your fill at the charming Irish joint Quays Pub (45-02 30th Ave at 45th St, Astoria, Queens; 718-204-8435) with rounds of Guinness ($5 to $6), poured just as they should be: in two steps, so that a perfect head peeks over the rim.

Sets you back: $22

Mansion Peeping
Photograph: Wikimedia Commons user 'Sterilgutassistentin'

Mansion Peeping

Start off an evening in Yorkville with an amble through Carl Schurz Park. Make sure to swing by Bobby Wagner Walk, a grand promenade along the East River, and Gracie Mansion (at 88th Street), the latest home of Bill de Blasio and official residence of NYC mayors.

Sets you back: Free

Brews, sweets and city views
Photograph: Virginia Rollison

Brews, sweets and city views

The inviting wood-paneling decor and dim lighting at Greenpoint drinking den TØRST make it a hot spot for old-timey romance. After sipping $6 drafts from local faves, head next door to Van Leeuwen Ice Cream for two small ginger, Earl Grey tea or other unconventionally flavored cones ($5.50 each). If the weather is nice, take your sugar rush to nearby McCarren Park, and sit on a bench facing the Empire State Building.

Sets you back: $23

  • Movie theaters
  • Independent
  • East Williamsburg
  • price 2 of 4

This overrated date night comes in handy, especially when the cost is dirt cheap. Unlike other movie theaters, Syndicated lets you wine and dine while you watch a classic flick. Get this: movie tickets are $7 apiece. And since the movie is so affordable, you can schmooze your date by splurging on some gourmet popcorn from the concession stand.

Sets you back: $7-$25

Bucolic strolls and cheap-ass tacos
Photograph: courtesy Central Park Conservancy

Bucolic strolls and cheap-ass tacos

If you’re looking to impress your companion by spouting off bits of horticultural expertise—hey, it might work—or if you’re just looking for a pretty spot in which to walk around and stare amorously into each other’s eyes, walk around the magnificent six acres that make up the Central Park Conservatory Garden. Once you’re done sniffing the magnolia and lilac trees, scoot over to El Paso Taqueria, where you can get two tasty tacos for $8.

Sets you back: $15–$18

    You may also like