This Boozy Hot Cocoa Is 20 Pounds
Ace BarAddress and Info
Remember that great Skee-Ball scene in Chasing Amy? You can reenact it here, hopefully with fewer surprising revelations! This place makes for a great first date if you want to avoid all of the so-where-did-you-grow-up questions in favor of getting competitive over bar games.
Museum of the Moving ImageAddress and Info
A film/TV museum is the kind of museum even non-museum-goers can get into: the Museum of the Moving Image curates a great mix of high and low culture, so you’re bound to find something you’re both interested in here.
Glorietta BaldyAddress and Info
This Bed-Stuy favorite has just enough close counter seating, candles, and dim lighting to be deemed “romantic” without being overbearingly so. Drinks are cheap, the beer selection is always great, and if you’re both craft beer nerds, the bar also hosts a beer trivia night. There are also pinball machines, should you and your date need some additional competition.
The Bowery BallroomAddress and Info
OK, going to a show may not be great for a first date, but if you’re on date three, or five, or 17, it’s a solid plan. Clearly which band you’re seeing matters the most, but the venue definitely factors in as well; you wouldn’t want to take a date to a show at the antiseptic Barclays Center, but you definitely want to take them to the Bowery Ballroom. It’s a fairly intimate space, and besides, if you get bored with the band, you can just head to the bar downstairs.
Boobie TrapAddress and Info
Taking your date to a boobs-themed bar might seem counterintuitive, but this punk dive is so playful (and lady-owned) that the second you set foot inside, you’ll both feel totally relaxed. Plus, it’s got the trifecta of board games, BBQ, and cheap beer. And you can color scantily clad ladies with crayons while you drink!
LeyendaAddress and Info
Star bartender Ivy Mix makes this Brooklyn hotspot the best space in the borough for cocktails. Try the jalapeño tequila-based Say Anything and ponder where John Cusack’s career has gone in the last few years.
The Golf Club at Chelsea PiersAddress and Info
It may seem a little cheesy, but a driving range on the water is actually the perfect afternoon date activity when you’ve exhausted matinee movies and picnics in Central Park (alternatively, if you want a good Sunday night date option that won’t leave you hungover on Monday morning, take advantage of the $30-per-person unlimited balls & club rental deal).
Nom WahAddress and Info
Brunch dates are a great idea, but bottomless mimosas and questionable eggs Benedict are probably better suited for a catch-up session with your friends than a getting-to-know-you meal. Switch things up by splitting a full dim sum spread (soup dumplings, pork buns, scallion pancakes) in a comfy leather booth at Nom Wah.
MayfieldAddress and Info
Once you and your date have moved past the “let’s meet for a drink” stage and are ready to consume food across from one another, the Southern-inspired Mayfield may be the perfect spot. It’s a charming, unfussy restaurant with exposed brick, plenty of seating, and casual but well-executed bites like cornmeal fried oysters and patty melts.
Amor CubanoAddress and Info
There are always bands playing, the bartenders make the best mojito in the city, and the ropa vieja and tres leches cake will make you question why you don’t spend more time in Spanish Harlem.
EastVille Comedy ClubAddress and Info
Making your date laugh with you is rarely a bad idea, and EastVille tends to get some pretty great acts in (hi, Janeane Garofalo!). Besides, if you go on a random night and the comics bomb, KGB Bar is right upstairs.
The Dead RabbitAddress and Info
The Dead Rabbit was just named the world's best bar (again), and for good reason: the cocktails are truly some of the best in New York, and possibly even the world (that includes the perfect Irish coffee). The drinks aren’t cheap, but if you’re looking for something a little more upscale for your date night, they’re a hell of a lot more affordable than the tasting menu at Per Se.
Brooklyn FleaAddress and Info
While it’s still somewhat warm out, spend an afternoon with your boo meandering this giant flea market, where you’ll find everything from old records to antique furniture to handmade crafts to locally made snacks.
Dear IrvingAddress and Info
From the team behind Raines Law Room, this speakeasy-inspired lounge is just as over-the-top as you’d want it to be -- sleek, cushy chairs hidden behind curtains; buzzers to call your waiter (like at its sister bar); and fancy drinks like the Night Café with genever, Aperol, lemon, egg white, and absinthe.
Milk and RosesAddress and Info
This space is so lushly romantic, the garden looks like Daisy Buchanan’s fever dream. In addition to idyllic surroundings, the Southern Italian food is also delicious: simple, fresh, high-quality ingredients that speak for themselves with little interference.
67 Orange StreetAddress and Info
67 Orange Street is a cozy, speakeasy-ish spot (you’ll pass through a velvet curtain to get in) known for its great craft cocktails and small plates. There’s always great music, but it’s never too loud, making it a perfect spot for a first or second date, when you want to actually hear the person talking to you.
Lower East Side
Nurse BettieAddress and Info
Sometimes you just want to take a girl to a burlesque show on a Wednesday night! The super-tiny, Bettie Page-inspired bar is full of flirty images of pin-up girls, a friendly crowd, and drinks that are both cheap and strong. But the real draw is the free burlesque shows every Wednesday and Thursday.
Long Island City
Penthouse 808Address and Info
Unless you’re dating someone who is just too jaded to enjoy a view of the city (left swipe left swipe left swipe), Penthouse 808 is pretty much guaranteed to be a solid hit. Grab some bar bites like tuna poke and rib-eye robata skewers and appreciate the sunset.
La BibliotecaAddress and Info
It’s hard to argue with an actual tequila library. In addition to all the tequila you could ever want, this candle-lit, leather-furniture-adorned spot offers plenty of great bar snacks, like charred tuna wonton tacos and spicy crab guacamole, and the happy hour special runs all night on Mondays and Saturdays, with $8 cocktails, $5 beers, and discounts on food.
Weather UpAddress and Info
It’s all about old-fashioned cocktails at this intimate Prospect Heights bar. While anything on the drink menu is a safe bet, opt for the Bartender’s Choice (you’ll be in good hands) and then grab a seat in the adorable back garden.
Housing Works Bookstore CafeAddress and Info
Housing Works often hosts great date-worthy events, but the space on its own is perfect for a coffee date. Plus, dollars spent here go to one of the best charities in the city -- Housing Works supports people living with HIV/AIDS.
Upper East Side
Steep Rock BoulderingAddress and Info
You can take a class together, or just try out the wall after a quick rock climbing tutorial. Plus, it's open until 11pm during the week, which makes this a surprisingly good after-work date if you didn’t have time to hit the gym that day (or if you want to pretend to be someone who “hits the gym” and notices if they miss a day).
Upper West Side
American Museum of Natural HistoryAddress and Info
The Natural History Museum is a great date idea if you’re nervous about running out of conversation topics -- wander the enormous halls scoping out dinosaur bones, gemstones, and a conservatory full of live butterflies together, and conversation will start to flow within about 45 seconds, promise. If not, blame the silence on the fact that you’re, you know, in a museum.
The CloistersAddress and Info
Unless you’ve been seeing a robot who hates pretty things, a picnic at the Cloisters is a pretty fantastic date: the gardens are beautiful, and the building itself is a medieval mash-up of five different abbeys that were shipped here from Europe. It’s basically as close as you can get to taking your date to France for the afternoon. Pour your wine into a POM bottle before you leave the apartment, and pack opaque cups.
The Rusty KnotAddress and Info
A surprisingly low-key find among the hoards of million-dollar high-rise apartments and expensive restaurants, The Rusty Knot is the perfect place to grab a casual Tiki drink and play a round of totally not-competitive pool.
Nitehawk CinemaAddress and Info
Nitehawk offers dinner during all its movies, which is terrific enough, but check out the Live Sound Cinema for something you won’t find anywhere else: musicians perform alongside silent films, which makes for a totally surreal experience.