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Meet the Undateables: Molly and Tom

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

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TK

Photograph: Ann Sullivan

Why they’re single:
Molly: She’s been focusing on family and friends for the past few years.
Tom: He’s single because of his general looks and personality.

Ideal date:
Molly: Grabbing dinner and then seeing some live music
Tom: Doing something a little weird that makes them both feel off-kilter

THE DATE

First impression
Molly: “He was sitting at the table, and the hostess directed me over. I was happily surprised to see him. I thought he was cute, and I liked his shirt. He seemed like a normal guy.”
Tom: “I showed up ridiculously early by accident, so I was waiting for a bit. She walked in, and I felt this wave of relief because she was attractive and seemed super chill.”

Chemistry
Molly: “For me, it’s difficult to know after just meeting someone once, but I know when I don’t like someone, and I don’t not like him. He’s definitely worth getting to know.”
Tom: “It started off with chemistry. By the end of the date, we developed physical chemistry. We had some flirty energy and kissed at the end. We talked about going out again.”

Awkward Moment
Molly: “We went to a bar after, and this guy on a barstool behind [Tom] was falling all over him. I was looking at the bartender, like, Can you help facilitate this?”
Tom: “We called him Blackout Craig. He fell on me—he was kind of hanging onto me, and he kept singing in the bar all night long. He was definitely the character of the night.”

Afterward
Molly: “We left the bar, and he asked me for my number and asked if I wanted to see him again. I said yes, and then there was a quick—very quick—kiss goodbye.”
Tom: “I had to wake up super early the next day, so we decided to head out. She called an Uber. We kissed before she got into it. It was a good old New York street kiss.”

Verdict

Molly: ♥ “It was a really good date. He was an easy person to hang out with and talk to. I think I’ll see him again, if he wants to. I would totally do it again.”
Tom: ♥♥ “It went super well. We talked about everything from weird fetishes to our crazy families and dating history. She was pretty, very relaxed and very fun.”

Our daters went to The Tuck Room (11 Fulton St, 212-776-8273)

Hear more about the date on Tom's podcast, The Undesirables.

RECOMMENDED: See more Undateables

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

Looking for a cheap date idea?

Desert Island
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

Photograph: Jakob N. Layman

Laughs and views

Start out an evening in LIC by sauntering through Gantry Plaza State Park, a waterfront respite that boasts a beautiful midtown-Manhattan backdrop. Next, head to double-tiered comedy venue The Creek and the Cave, which welcomes stand-ups (including occasional surprise bigwigs like Jerry Seinfeld), improv troupes and variety shows every night of the week, often for nada. Prove that you’re not that much of a Costanza by springing for some fish and pork tacos ($4–$6). 

Sets you back: $12–$15

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Pete's Candy Store, live music venue, Williamsburg, Brooklyn

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

Syndicated, dine-in movie theater
Photograph: Courtesy Michael Tulipan
Movie theaters, Independent

Dinner and a movie

icon-location-pin East Williamsburg

This overrated date night comes in handy, especially when the cost is dirt cheap. Unlike other movie theaters, Syndicated let’s 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

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Restaurants, American

Hot-and-heavy at Alameda’s happy hour

icon-location-pin Greenpoint

This Greenpoint bar knows how to set the mood with rustic wooden tables and romantic lighting without making you go, y’know, broke. Hell, you and your date can get a buzz and some grub for 11 or 12 bucks! You can’t go wrong with a classic beer and burger deal or something a little fancier like boquerones and Prosecco.

Sets you back: $11–$12

Photograph: Courtesy Caroline Voagen Nels
Bars, Pubs

Get your groove on at midnight

icon-location-pin 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

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Four & Twenty Blackbirds
Photograph: Lizz Kuehl

Dessert and mind-blowing 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’s monthly Secret Science Club event, where experts lecture on crazy-cool theories for free. Tip: Bring someone geeky to this, lest you seem…like a total geek.

Sets you back: $11.50

Van Cortlandt House Museum
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

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A cinematic shrine and plenty of Guinness

Secure film-buff status by bringing your date to the Museum of the Moving Image on a Friday evening (4–8pm), 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

Experimental theater and suds

Take that cute starving artist to The Chocolate Factory, which hosts cheap ($15 to $20) and free avant-garde theater, dance and performance art. If you opt for a gratis show, treat yourself to libations at the roomy craft-brew haven Alewife Queens and have a deep conversation about the meaning of the work you witnessed. Get more bang for your buck by splitting a growler of the 7.2 percent ABV Beerly Legal Saison, brewed specially for the owners by Captain Lawrence.

Sets you back: $30–$50

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