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Josh and Shannon

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
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TK

Photograph: Ann Sullivan

Why they’re single:
Josh: He was recently in a nine-year relationship and is thinking about taking a break from dating.
Shannon: She doesn’t have a typical nine-to-five job, so it’s hard to find time to go out.

Ideal date:
Josh: Going to a cool and quirky bar, followed by a surprise activity
Shannon: Barhopping at local speakeasies

THE DATE

First impression
Josh: “I got there on time; she was a little late. With so many dates I’ve been on, they’ve always been a little late. I try to make it on time. It didn’t bother me, though.”
Shannon: “I noticed right away that he was English because of his accent. He seemed smart. Personality-wise, he was my type, but he wasn’t someone I’d pick out of a crowd.”

Chemistry
Josh: “The conversation flowed well.  One of her clients is Lance Armstrong, and I think I’m the only person left in America wearing a Livestrong band, so that was pretty fun.”
Shannon: 
“I think there was friendly chemistry. He knew a lot more about American sports than I would have guessed! That was nice. I think both of us appreciated the conversation.”

Awkward Moment
Josh: “She only used her fork to eat her salmon—no knife. That’s something that stuck with me, but maybe that’s because I grew up in more of a formal British setting.”
Shannon: “I don’t usually get asked on a first date how long I’ve been single, so that was a little different. That caught me off guard a bit; I wasn’t prepared to answer that.”

Afterward
Josh: “She said she wanted to go to bed early, and I was like, ‘I assume you don’t want to get another drink,’ but then she was like, ‘I’m down!’ So we went to a second bar.”
Shannon: “We went to a bar down the street, but it got kind of late so I decided to head home. We exchanged numbers, hugged, and then I went home. I feel like we both had a good time.”

Verdict
Josh: ♥ “It was the base level of what I consider a good date. It was fun but not that memorable. I’d give her the benefit of the doubt if she wanted to go on a second date.”
Shannon: ♥♥♥ “He was a great guy. I feel like we had a good, friendly chemistry. If he wanted to go out again, I probably would, but I’m not sure if either of us was really feeling it.”

Our daters went to Bell Book & Candle (141 W 10th St, 212-414-2355)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email undateable@timeout.com.

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

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  • 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

  • Bars
  • 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)

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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 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
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 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

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

Sets you back: $20

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 anthology.

Sets you back: FREE

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Cans o’ beer and lush gardens
Photograph: Courtesy Marlborough Gallery/Richard Estes

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
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/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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