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Fun dating new york 49 Actually Great New York Date Ideas, Sorted By What Date You're On

Published On 10/16/2014 Published On 10/16/2014
couple on the Brooklyn Bridge in New York
oneinchpunch/Shutterstock

Look, we don't know your life. Maybe you're a novice who's never planned a date past a dinner reservation and a clean shirt, or maybe you're a Dating Grandmaster who hires hot-air balloons the way other dudes hire Ubers. Regardless of how your dating expertise stacks up, you know that the city offers more date-ventures than dinner and drinks, drinks and dinner, and more dinner and more drinks.

So, to help you mix it up, we culled a list of the 49 best dates you could possibly take someone on in NYC, and sorted them all by which date (first? third??) you should use them on.

Royal Palms Shuffleboard Club

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Gowanus
A worthwhile date in Gowanus used to be practically impossible (What is the point of online dating sites are completely free will do that), but that was before The Royal Palms showed up. Enjoy the cocktails on tap and try your hand at a game and you’ll understand why your Grandma and every hipster in Brooklyn loves it so much.
 

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Lenox Hill
The California sea lions balance balls, catch fish, and interact with their trainers in the cutest ways possible, and their glass-walled enclosure gives visitors a great view of all the action. Go for a walk in the park after, or stick around the zoo and check out the red pandas because, well, they're adorable.
 

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Williamsburg
Swing by Who is diggy simmons dating 2016 for dollar oysters any Monday through Saturday from 6-8pm when you can get a mix of East and West Coast specimens. Also, the short-term nature of a happy hour gives either of you an out if a better Tinder match comes up.
 

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DUMBO
That refurbished carousel in Brooklyn Bridge Park is kind of endlessly romantic, plus there are a bunch of great dinner options within an easy walking distance: the delicious tequila cocktails at are just around the corner and don’t require a Grimaldian wait.
 

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Crown Heights
For some reason, when you put an ingredient like rum into a cute milkshake glass, it just feels wholesome. This place is genuinely adorable, and even has vegan options, in case that Bumble cutie doesn’t do dairy.
 

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Upper East Side
With one of the lushest lawns in the city, the Met’s roof garden is a perfect little oasis in the center of the crowd.
 

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Crown Heights
This place may actually be better to visit during the winter than the summer -- especially the hothouses, which are kind of like taking a (sadly overdressed) trip to Costa Rica. Oh, and make sure to tell your date about how the Japanese garden contains a hidden temple dedicated to the wolf spirits.
 

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Williamsburg
Free skee-ball and $5 well drinks during Sunday happy hour = cheap date with a super fun distraction. It’s also a good date-that-doesn’t-feel-like-a-date, in case you’re feeling things out...

Manhattan by Sail

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Midtown East
Sneaking into an indoor pool is a great, slightly illicit date for all seasons, and it’s surprising . The One UN is a cakewalk, though: just stroll with purpose to the elevator in the East Tower, pop up to the 27th floor, and glide right into the locker room, which is the pool’s access point. Worst case scenario: pretend you’re confused representatives from Estonia. Nobody will be the wiser.
 

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White Hall
Unlike the first date, you should be reasonably sure you want to spend some time together, so sign up for , which'll include a couple of hours sipping ales, nibbling charcuterie, and taking in the skyline views.
 

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Bushwick
Hit up the only mini-golf course in town that comes with pickleback shots, and don’t forget to pack your own clubs for this misadventure.
 

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Lower East Side
On Tuesday nights, burlesque venue The Slipper Room turns into a comedy show hosted by Seth Herzog, usually accompanied by his completely awesome -- and deeply hilarious -- Mom. Don’t let your date know in advance, but there’s a fairly high chance that a celebrity or two might show up.
 

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Midtown
Enjoy the unusual sensation of eating lunch beside a relaxing waterfall in the center of Midtown Manhattan, just one of the many in the city you can introduce your date to.
 

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Harlem
at a little venue called Shrine. This place (which looks kind of like a bodega on the outside) offers outstanding shows pretty much every night of the week.
 

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Williamsburg
Normally we wouldn’t encourage you to go to a lecture on a second date (... or any date, for that matter), but trust us, these things tend to be more hilarious than informative. In between sipping drink specials, local storytellers give short, themed lectures to a surprisingly rowdy crowd on subjects like “Wars Over Animals and Inanimate Objects,” “The Story of Stripping,” and “Ain’t No Party Like a Donner Party.” Show up on time to snag a table (and a bottle from the bar).
 

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Midtown
This is a solid choice even if you’re a novice paddler: offer super-easy tours that involve snacks and don’t require strenuous work or upper body strength. If you’re both feeling like a workout, however, you can sign up to paddle all the way around the city or out to the Statue of Liberty.
 

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East Village
This one works best for a date who’s recently relocated to the city -- most people who live in New York have already been here (which makes the bar no less special, but, you know, lessens the surprise a little). Watch their disappointment at getting taken to a hot dog joint dissipate into gleeful surprise as you make the big reveal...

Mehanta Bulgarian Bar

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East Harlem
Start off at , a standing room-only joint with the best -- and some of the cheapest -- tacos in the entire city (we defy you to spend more than $10 in this place), then mosey over to for mojitos and desserts.
 

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Upper East Side
Head over to  to try it out together. They don’t take reservations, but someone is always around to give you a quick tour before setting you loose to figure out how to climb walls. Surprising bonus: it's open 'til 11pm on weekdays.
 

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Hunters Point
On Sundays, the museum offers up a live presentation, which may be anything from dance exhibitions to short films to musical collaborations. These performances are recent works by contemporary artists, dusting some of the must off a typical museum date.
 

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Financial District
The round-trip boat ride itself -- and view of Lady Liberty -- is well worth the trip (plus, there's a bar on it), but the Staten Island offers some pretty amazing gems: Staten Island is something special,  offers two-for-one drinks and free pizza at the bar during its 4pm-7pm happy hour, and is unlike any other restaurant you’ve ever been to: a rotating cast of Italian grandmas take over the kitchen, cooking up their favorite regional specialties.
 

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Lower East Side
is some strange magic: this place combines Slavic music, a dance floor, and an ice cage. You and your date can shrug on gigantic overcoats (provided), and enter a freezing room made of ice for two minutes' worth of unlimited shots. 
 

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Williamsburg
The most classic date of all can be a little too obvious. Mix it up a bit with 's , wherein a live band plays against a silent film.
 

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Chelsea
The 9:30pm Sunday night show is free, but be sure to swing by in advance (around 8:15pm) to snag tickets, as they tend to run out. The performances at this long-form improv show feature some of the funniest people in comedy, frequently including writers from SNL and The Colbert Report.
 

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Washington Heights
Surprise your date with your knowledge of the gorgeous views uptown, and with a well-appointed picnic.
 

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Marine Park
This place was the  and makes a great daytime date: explore abandoned hangars, scope out the nature trails, check out their collection of antique planes... even go horseback riding.
 

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Gowanus
Bring a thermos full of mimosas to help you handle the long-ass line, but trust us, this semi-regular flea market is weird and amazing enough to be totally worth it. Not to mention the exquisite people-watching opportunities that abound here.

Flickr/Toni Protto (Edited)

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What better way to celebrate an excellent third date than by finger-brushing your teeth, smoothing out your outfit, and hitting up one of the city’s ?

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Williamsburg
The brewery offers free, regularly-scheduled tours every Saturday and Sunday (and they’re only $15 Monday-Thursday). Your opening material is running thin at this point, and this'll fill any silences nicely. So will the beer.

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Lower East Side
You’ve already been to the dance parties at , but you may not have checked out its awesome ground-floor burlesque show.
 

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Chelsea
Pop in for a drink at , where you can share your knowledge of how people are often caught having sex in windows of The Standard.
 

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Brighton Beach
Known as “Little Odessa", Brighton Beach has maybe the best Russian food in the Western hemisphere. Snack on some of the ever-present traditional baked goods (available on basically every street corner), then settle in for a proper meal at  or enjoy .
 

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Lower East Side
This dive offers a great craft beer selection, an awesome happy hour special, and an unusually quiet back room to chat with a date on a weekday.
 

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Bushwick
Graffiti shop by day, gallery by... well, also day, but also the occasional evening. Come out for an art opening and introduce your date to the awesome street art, PBR, and creative vibe.
 

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Bushwick
Get competitive over Candyland in this fun, totally lady-friendly (and woman-owned) jugs-themed bar. Everything in the small space is covered in boobs, boobs, and more boobs, but the atmosphere is playful, really! Try coloring in mildly dirty cartoon pictures with crayons while you wait for a plate of their extra-delicious barbecue.
 

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Chinatown
If you’re into learning and drinking (remember college?), then you may want to spend a Saturday making and sipping high-quality drinks from the pros. The courses at vary from classic cocktails, to the garden-to-glass variety, to absinthe-bases.
 

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Riverhead
Okay, it’s kind of a hike, so you have to be comfortable enough with each other already to train it, but if getting up close and personal with a penguin sounds like your idea of a good time (and your basic humanity should be questioned if it doesn’t), then consider this a good time.
 

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Multiple locations
OK, it’s not technically flying, but it’s probably the closest you’re going to come in your sadly wingless existence. Just make sure your new sweetie doesn’t have a massive fear of heights before booking this one...

Sleep No More NYC

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Financial District
So this may be a little pricey, but this is "are we in a relationship or what?" territory, so splurge. It’s the only way you’re ever going to see the city in that epic 365-degree view the way you do in movies, and it makes for one adrenaline rush of a date. 
 

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Little Italy
offers one-off cooking classes: try out the butchering demo and masterclass, where you learn to prepare things like "a whole grilled grass-fed lamb", or try out one of their delicious -- but less intense -- Italian, Spanish, Indian, or French cooking courses.
 

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TBD
Yeah, you read that right: go on one memorable pre-work date at , the rave that starts at 7am. Throw back some espresso shots and get down on the most unlikely dance floor in the city during the time you’d normally be hitting the gym -- .
 

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Lower East Side
Not for the faint of heart, offers intriguing ideas (and an array of fun toys) for getting frisky, from oral sex tips to spanking, in a regularly scheduled brunch-time lesson (comes with free muffins!).
 

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Elmhurst
Yeah, yeah, they’re really cute, but they’re also high in protein, low-fat, and totally tasty. Get adventurous and try out this staple of Peruvian cuisine at El Dorado Café.
 

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NoHo
Learn all about the culture in New York during the Roaring Twenties, and stop by some of the country’s most notorious speakeasies. Tours with tend to sell out in advance, so book this one about a week out. Packing a flask, while not encouraged, is simply in keeping with the theme.
 

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Flatiron
MoSex is often funny, sometimes clinical, always fascinating, and kind of less erotic than you might expect. But it’ll definitely open up more intriguing conversations between you and your date, and after a tour, you can share an aphrodisiac drink and the self-proclaimed best sticky bun in New York in the .
 

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East Village
This Village staple offers readings nightly, but the Monday Night Poetry series stands out. The venue has a full bar, so even if you’re not in love with the poet at hand, you can enjoy a good whiskey, then discuss the details with your date after.
 

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Multiple locations
There are so many parks in New York that , but even make grills available for this very purpose. Invite some of your friends and let them mingle -- come on, you’re five dates in, you might as well get to know each other’s people.
 

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Times Square
Hit up a , buy whatever tickets are the absolute cheapest, then kill time before the show with a Guitar Hero tournament at .
 

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Chelsea
Look, if you do Sleep No More together on your fifth date, the immersive strangeness of the experience is going to mean that you’re either dating or you’re about to stop seeing each other. If you’re OK with that gamble, then go forth.

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’s dream date somehow involves French bulldog puppies, whiskey cocktails, and skee ball. Follow her on Twitter at and Instagram at

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