Sarah and James

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

Will Gleason


Photograph: Ann Sullivan

Why they’re still single:
Sarah: She’s really busy and enjoys the single life.
James: With his schedule, he’s usually only free late at night.

What they learned from their last Undateables date:
Sarah: If you go in with zero expectations, you’ll feel a lot less nervous.
James: It’s easier to talk to someone who is following their passion.


First impression
Sarah: “I thought he was really nervous and kind of shy. He stumbled over his words a lot. He was really sweet, but it just took a while for him to get into the conversation.”
James: “She was nice, but I didn’t have much to talk about with her. Once she knew I worked in the theater, she only wanted to talk about famous people I’ve worked with.”

Sarah: “I wouldn’t say there was much chemistry—it was a pretty basic conversation. We talked a lot about things to do around the city. He grew up here and had great recs.”
“I couldn’t get a read on her, so it was hard for me to tell what she was looking for. Also, she didn’t know where Flushing was, even though she’s been to a Mets game.”

Awkward Moment
Sarah: “We were at a cocktail bar with 25 different, really cool cocktails on the menu, and he ordered a rum and coke. I gave him a hard time about it, but I was just kidding.”
James: “She kept apologizing for liking basic things, and I was like, ‘I don’t care if you like Taylor Swift or Ariana Grande! That’s fine! Why are you apologizing to me? I’m just a man you met in a bar.’ ”

Sarah “He asked if I wanted to do this again sometime, and I said I wasn’t really sure. He was going to take the same subway as me, but then he said he was just going to walk.”
James: “To be polite, I asked her if she wanted to go out again. She said no but then said she’s never been asked out on a second date before. I thought that was strange.”

Sarah: ♥ “He was really sweet, a total gentleman. As a date, it was great, but there wasn’t really any chemistry. From the last date to this one, we’re moving in the right direction.”
James: ♥♥ “I’ve had better dates. I would go back to that bar with someone who I really liked, though. Actually, there’s someone else I really like that I might take there.”

Our daters went to The Up & Up (116 Macdougal St, 212-260-3000)

RECOMMENDED: See more Undateables

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

Looking for a cheap date idea?

  • Sports and fitness
  • Sports & Fitness

If your date can't volley some jokes while gently hitting a plastic ball across the table, well, maybe that's a foul. See if you two hit it off over a game of table tennis at Ping Pod. These 24/7 ping pong pods are popping up all over NYC. Pricing ranges from $15-$50/session depending on demand (be sure to book online in advance).

We recommend trying the Astoria location so that after you've worked up an appetite, you can walk a few blocks to The Freakin Rican for one of the city's best cheap eats: The $4.25 alcapurrias. 

Set you back: $25+

  • Museums
  • Art and design
  • The Bronx
  • price 1 of 4

Grab some lunch at 188 Bakery Cuchifritos in the Bronx, a casual lunch counter focusing on all things pork with recipes of Puerto Rican and Dominican provenance. Cuchifritos are the fan-favorite, the standout morcilla (aka blood sausage) in particular — and it's only $2.

Then, head a few subway stops uptown to the Bronx Museum of the Arts where you can see more than 1,000 works of art and imrpess your date with just how cultured you are. The Bronx Museum of the Arts is always free to visit. 

Set you back: $15

  • Attractions
  • Parks and gardens
  • Chelsea

Stroll The High Line with your sweetie, a place of respite among the concrete jungle. While this spot is most popular during the warm months, its fun to visit any time of year. 

Don't miss the rotating works of sculpture and art by different artists every season. Also keep an eye out for free star gazing nights and lively cultural happenings like Latin dance nights. The best part, however, has to be the people watching: Grab a seat on the stairs over looking busy Tenth Avenue and see locals and visitors from all walks of life milling their way about the city.

Set you back: FREE

  • Breweries
  • Williamsburg

If you and your sweetheart are major beer enthusiasts, Brooklyn Brewery hosts an intimate tour (no more than 30 souls), where you can geek out and get an exclusive look around the joint. The informative guide not only gives you an in-depth history lesson about the brewery, but a beer tasting along the way.

And you won’t walk away empty-handed either: all participants leave with a complimentary souvenir glass, so you’ll have a little something to remember the date by (besides the hangover.)

Sets you back: $48+ (tours start at $24/person)

  • 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 just $9 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: $18+

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 cost about $12. (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 for a free dance party or a show like Secret Science Club. Tip: Bring someone geeky to this, lest you seem…like a total geek.

Sets you back: $12

  • 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 ($7) or wings ($13)—served until midnight —before you hit the dance floor.

Sets you back: $20

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 anthology.

Sets you back: FREE


Cans o’ beer and lush gardens

Enjoy the city’s cheapest booze cruise and panoramic views of lower Manhattan aboard the Staten Island Ferry, where domestic cans are in the $5 range.

Once ashore in Staten Island, take an eight-minute bus ride and tour the grand estates and lovely waterfront grounds of Snug Harbor Cultural Center and Botanical Garden, originally established as a retirement estate for sailors in 1801. Tickets cost $5/person.

Sets you back: $30

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/person), 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

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