We Planned 15 Perfect NYC Dates – So You Don’t Have To

There are so many “date ideas” lists out there. You know, like “10 Unique First Date Ideas” or “6 Date Ideas to Bring the Romance” or “Creative Date Ideas” (to name a few from the Google search I just did!).

But all of these require so much work and research! Sure, it sounds fun to go to a bar that has live bluegrass, but which ones even do in my city? And if I haven’t been there myself, how do I know if it’s going to be the vibe that I want? Can’t someone just tell me exactly what to do and where to go? What are the best dates out there??

As you know if you’ve followed me for a while, I went on nearly 100 dates before meeting my partner, and let me tell you, I did NOT have the bandwidth to research and plan cool, stand-out experiences.

So now, I’m going to do it for you!

Style My Profile is going to release lists of specific, unique date ideas by city, and we’ll take all the guesswork out of it by telling you exactly where to go and what to do.

First up: the best New York City dates! (of course!)

Myself or someone on the SMP team has personally been on every single one of these dates (and can vouch that they went WELL 😉). So if you’re looking for fun date ideas in NYC, look no further…

NYC Art Dates

A classic date: strolling through a museum and grabbing a cozy drink afterwards to discuss. Museums and galleries give endless conversation fodder – your impressions of the art, ranking favorites, telling stories the art reminds you of, showing off any tidbits you remember from that Art History class back in college, people watching in the galleries, the list goes on. Here are some of our favorite spots paired with a bar to set the right kind of intimate discussion vibe for after you’re all museum-ed out.

The Met + AOC East

The Met can be daunting, so keep it manageable – pick 2 galleries you want to see ahead of time so you have a bit of a plan and don’t get overwhelmed by choice (bonus points if you and your date each pick a gallery you think the other person would like!). AOC East is a cozy French wine bar only a few blocks away. Think brick walls, candles, and tables that don’t make you feel like you’re sitting a mile away from your date (so you might just *accidentally* brush knees).

Brooklyn Museum + Tooker Alley

The Brooklyn Museum is like the funky cousin of The Met. A lot of the art is larger than life, and practically begs for commentary. (If you’re feeling up for a particularly ~interesting~ conversation with your date, check out The Dinner Party.) Head two blocks away to Tooker Alley for a date-y atmosphere, an extensive and inventive cocktail menu that doesn’t take itself too seriously, and live music if you’re lucky.

Chelsea Galleries + Porchlight

You can hardly take 10 steps in any direction on any blocks 19th-27th Streets between 10th and 11th Avenues in Chelsea without hitting a world-class contemporary art gallery. For a chic weekend date (since most galleries close at 6pm), swing by two that are guaranteed to have unmissable exhibitions: David Zwirner on 19th and Gagosian on 24th. Afterwards, stroll over to Porchlight, a cocktail bar that feels like a cross between a ski chalet and an apothecary.

NYC Comedy Dates

I used to make it a rule that I’d see a comedy show on a third or fourth date – I always wanted to see whether our specific senses of humor aligned and we’d laugh at the same things, what they were like as an audience member, whether they had a charming or annoying laugh, etc. Comedy abounds in New York, but here’s a Manhattan and Brooklyn recommendation (plus a bar pairing) that has always reliably given me and the SMP team the best laughs.

Comedy Cellar + Dante

The Comedy Cellar is arguably the hottest comedy ticket in town due to their high-caliber humor and near-constant celebrity comic drop-ins, so you’ll want to grab tickets a week or two in advance. Shows are on the later side, so stop by Dante on MacDougal St first for their buzzy chic-Italian-cafe atmosphere and Negronis – one of my personal faves – on tap (on tap!!).

Union Hall

You get a 2-for-1 deal out of Union Hall in Park Slope – a cozy bar on the main floor that feels like drinking in your grandfather’s study (leather chairs, walls of bookshelves), and a downstairs stage that hosts intimate comedy shows every night of the week with a rotating cast of Brooklyn’s best stand ups. Union Hall also has two shuffleboard lanes in the back, so you can show off your competitive side.

NYC Theater Dates

I mean, you can’t think of New York without thinking of theater in some capacity. A dinner date alone is great, but throw seeing a play in the mix and you’ve really got a date worth writing home about. I love a good Broadway musical, but on early dates I actually prefer going to one of the reliable Off-Broadway theaters for a more intimate, less grandiose experience. My insider tip (from an SMP team member who doubles as an actress herself): download the TodayTix app, which has daily lotteries you can enter for $20-30 tickets to lots of the Off-Broadway shows. Enter a handful of the lotteries and see where you get lucky! And if you’re not a lottery winner, just get tickets for whatever’s showing at Playwrights Horizons – I’ve never seen a show there that wasn’t memorable, exciting, and beautifully written and acted. Pair it with dinner at Bea, a lovely, airy spot that is probably the only theater district restaurant that I would put on this list 😉

NYC Music Dates

I could write an entire newsletter on New York music venues and still not be able to cover all the great scenes and options. But for an early date, two types are my go-tos.

Jazz in the West Village

With fall and winter around the corner, sometimes there’s nothing better than cozying up with some live music – and there are few better than a classic West Village jazz spot. While it’s hard to go wrong in the neighborhood, Village Vanguard stands in a class of its own. To start, you can easily grab tickets on their website, to avoid trouble getting a table on the night of your date. They also list the musicians for all of their upcoming shows, making it easy to listen to each one ahead of time and be sure that it matches your ideal vibe. Finally, sets are only about an hour – which leaves you plenty of room to grab dinner beforehand, or hit a bar afterward to debrief the show.

SoFar Sounds

Here’s what happens when you sign up for a SoFar Sounds concert. You choose which date and which neighborhood works for you (there are multiple concerts every night across the city). The exact location is revealed to you 2 days before the concert. It might be an office rooftop, someone’s living room, a loft space, or a backyard – intimate venues that might have 25 people in attendance or 80, you’ll find out when you arrive. 3 surprise artists or groups will perform sets in an atmosphere that’s overwhelmingly inclusive, friendly, and low-key. Often you can bring your own snacks and beverages, often you’ll find yourself sitting picnic-style on blankets and pillows on the floor, and almost always you’ll strike up conversations with the other concertgoers around you. A perfect date for friendly, easy-going music lovers of all ages.

NYC Date for Book Lovers

If you’re a reader, you know there’s nothing as energizing to talk about on a date as book recommendations. Loving and hating the same books is practically a fast-track to falling in love (as one of my coaches can attest, after spending the first hour of her first date with her now partner of two years running through their Goodreads lists). If words are the way to your heart, look no further than these book-centric dates.

Book Club Bar

Book Club Bar is my favorite hidden gem nestled in the East Village. Coffee shop by day, wine bar by night, and book store all day long, this is an unbelievably cute, cozy date spot if you want to browse curated shelves of all the latest and best contemporary books and then discuss your reading recs over a glass of wine at the bar in the front. Charm level: 10/10.

Author Talks at Books are Magic or The Strand

Speaking of charming book stores, look no further than The Strand in Flatiron, arguably New York’s most iconic book store, or Books are Magic in Brooklyn, as magical as the name implies. Both of these host talks nearly every night with popular authors, consisting of an incisive guided interview and the opportunity for audience Q&A. It doesn’t matter whether you’re a longtime fan of the particular author or have never read their work – you and your date are guaranteed to learn something, get great new recommendations, and have so much to discuss. Afterwards, grab a cocktail at Cibar near The Strand or Leyenda near Books Are Magic.

NYC Active Dates

For the New Yorkers out there who hate sitting still, get your blood pumping a bit with these dates that’ll have you exploring NYC in new ways.

The High Line + Ice Cream

I’ve always been a champion of walking dates – conversation often flows even more naturally when you’re side by side, and able to remark on all that’s around you – especially when the walk has a clear beginning and end. The High Line on a beautiful day is the best of the best, filled with fascinating rotating art installations and gorgeous city views. Add an ice cream cone and you’ve got the purest date of all time. The High Line is peppered with various food vendors, but I personally recommend Malai at 22nd St. (try the Red Chili Chocolate or the Masala Chai).

Little Island + Market 57

Little Island: New York’s cool new pier on the West side you keep telling yourself you’re going to go to, but never do. So explore it on a date! Take in the views, walk the winding paths, marvel at the unique concrete “tulips” holding up the lawns, and, in the summers, take in the daily free programming at the amphitheater. Watch a glorious sunset over the Hudson and then sample an array of international food exclusively from minority- and women-owned businesses at the Market 57 food hall.

Pickleball + Pizza

Have you joined the pickleball craze? If you have, you know it’s a sport you can do at any age, and that it is wildly addictive. Purchase a couple of paddles and then head to Pier 2 in Brooklyn Bridge Park, where there are 4 free courts open all day long. Players stack their paddles in a row to keep track of who’s next in line for a court, and you and your date will be competing against whoever’s paddles are stacked next to yours. The community of pickleballers there are overwhelmingly friendly and inclusive, so you and your date may find yourselves making new friends while waiting for your court. When you’re all pickled out and ready for pizza, stroll down to Fornino on Pier 6 for rooftop dining under twinkly lights, the Manhattan skyline in front of you.

Red Hook Date

Picking a neighborhood and making a whole evening of exploring it (or a whole day!) is one of my favorite things to do in a city as diverse as New York, either on an early date or with a partner of many years. A lot of neighborhoods have Instagram accounts to help you plan your journey by seeing what catches your eye – @greenpointers and @cobblehillcollective are a couple of my favorites in Brooklyn. But to feel like you’re transported out of the bustle of New York City and into a quaint seaside neighborhood, look no further than Red Hook.

Start early with competitive games of corn hole and some seafood appetizers at Brooklyn Crab’s beachy front yard. Choose your own adventure for dinner: brave the line at Hometown BBQ for barbecue that rivals any in the South, or gorge yourself on what might just be the best burger in all NYC at Red Hook Tavern (snag a reservation well in advance, or put your name in early and grab a drink at divey, homey Docky’s across the street so you can easily pop over and check your progress on the waitlist). Next, stroll over to Strong Rope Brewery or Red Hook Winery, both of which boast to-die-for views of the Statue of Liberty (sunset is peak time). The required final stop of the night is Sunny’s, a cozy cash-only bar that is the heart and soul of Red Hook. Live folk and bluegrass comes on every night at 8, and it’s not to be missed.

I hope this list is helpful to you and inspires countless memorable NYC date nights 😊 Any types of dates I missed that you’d be interested in? Any cities where you’re dying for recommendations? Any recommendations YOU have, that I can add in a follow-up post? Email me and let me know!

Happy Dating!


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Hi! I’m Alyssa Dineen and I’m a personal stylist and dating coach all rolled into one. I started Style My Profile to help other online daters feel better about getting out there— and staying out there— in the world of online dating. Whether it’s to meet your soulmate, to find a fun person to have dinner with or even just match with more people, I can help you from the ground up.


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Purchase our Profile In An Hour, designed for getting your profile swipe-right ready in as little time as possible.