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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
Written by
Will Gleason
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TK

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.

THE DATE

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.”

Chemistry
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.”
James: 
“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.’ ”

Afterward
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.”

Verdict
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 undateable@timeout.com.

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

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  • 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

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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

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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

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  • 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

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