Matt and Caitlin

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test

Will Gleason
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TK

Photograph: Ann Sullivan

Why they’re single:
Matt: He doesn’t want to settle for someone who’s below his high standards.
Caitlin: She’s always busy, but when she has free time, she just wants to be with friends.

Ideal date:
Matt: Drinks in a dive bar with a relaxed environment where you can talk easily
Caitlin: Going to a hole-in- the-wall restaurant and then walking across the Brooklyn Bridge 

THE DATE

First impression
Matt: “She wasn’t particularly my type, but I didn’t want to write her off immediately. But on a simple eye test, I wouldn’t say she was someone I would necessarily swipe ‘yes’ on.”
Caitlin: “He was really cute and polite and acted interested in me. Neither of us dominated the conversation. He seemed really respectful. I could tell he was a little nervous.”

Chemistry
Matt: “It felt more friendly than anything else. There was little to no romantic element at all, which was probably from me initally being like, ‘Nah.’ But it was a nice conversation.”
Caitlin: 
“I could see us being friends—we have a lot in common. We’re both family-oriented and have younger siblings. He was just genuinely nice and seemed totally normal.”

Awkward Moment
Matt: “At one point, I knocked a chopstick in the air. It was up there for a couple of seconds, then it landed on the ground. That was me being graceful. We laughed it off.”
Caitlin: “He ordered shishito peppers, and I’m not good with spicy. I ate an especially spicy one, and it was so hot, I started tearing up and dropped the stem into my water.”

Afterward
Matt: “We exchanged numbers and hugged it out. I’ll probably text her, but from a ‘Let’s go out again, just the two of us’ standpoint, it’s gonna be a no from me, dog.”
Caitlin: “We did a cute hug and exchanged numbers and last names. He was like, “Hopefully we’ll talk soon!” I texted him a couple of hours later, and he texted back.”

Verdict
Matt: ♥ It was a fine evening of nice conversation. She was perfectly lovely, and I have nothing bad to say about her. She just wasn’t the right person for me.”
Caitlin: ♥♥♥ “I’m very open, and I could tell he was more reserved and shy. I’m not over the moon, but he was a really nice guy. I would go on a second date with him.”

Our daters went to BòCàPhê (222 Lafayette St, Nolita, 646-882-1939)

RECOMMENDED: See more Undateables

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

Looking for some cheap date ideas?

  • 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 $4.50 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'll only cost you a few bucks.

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 stargazing 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

  • 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+

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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

  • Sex and dating
  • Sex & Dating

Hold hands as you walk through The Met on a night at the museum together. Become acquainted with each other—and the artwork—during informal drop-in gallery chats, the chance to listen in on gorgeous live music and sip on yummy cocktails.

Events are free with museum admission, which is pay-what-you-wish for New Yorkers.

Budget: It's up to you

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  • Pubs
  • Park Slope

No matter how tight your budget, you can still get loose on the dance floor at Park Slope's Union Hall. Keep an eye out for free dance parties, 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

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

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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

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) 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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