Unusual Date Ideas to Try in New York City

Couples often put on weight once they start staying in more, sharing bottles of wine and pizzas. Get off to a good start by booking a small-group guided running tour through Central Park. If you’re not super-fit, the incentive will be learning about the city’s architecture and urban planning. You’ll pass famous sights including the Dakota Building and Strawberry Fields (a quiet space dedicated to John Lennon, who was murdered outside his apartment in the former in December 1980) to the central woodland known as the Ramble.

Bryant Park is a year-round quintessential NYC destination famed for its lush gardens and range of free activities, all surrounded by some of the most magnificent skyscrapers of Midtown Manhattan. New Yorkers love this park, and the laid-back local-feeling nature makes it the perfect date space, whether you join a morning tai chi class, take a birding tour or combine cardio with artistry – believe it or not for some ribbon dancing.

If you’re a bit strapped for cash, go the original route. Sofar Sounds are free live-stream performances in the Sofar listening room (optional donations can be given directly to the featured performing artists). Featured artists include some Grammy-award nominated biggies as well as lesser known names, and the music spans jazz-pop to country. Snuggle up on your hotel or apartment sofa (r) and tune in.

Feeling the need for something sublime? Channel your spiritual side with a trip to Magic Jewelry, a cult-classic in Chinatown. Specialising in feng shui and an in-store aura photo and reading service to reveal the colors of your energy field (electromagnetic field), they also sell intricate (and not so cheap) jade jewellery and custom-made crystals.

Keep things intimate and less showy and go see an off-Broadway show with your date. The great thing is that major productions can be seen here before or after they hit Broadway proper – we’re talking the likes of Stomp and Jersey Boys to Sistas and The Play That Goes Wrong. You won’t pay as much as you will when they transfer, and you can choose comedies, musicals and plays, depending on how you want to impress your date – humor first, or intellect?

Seek out the city sights and play tourist for the day. Be honest, have you really explored every tourist attraction in your hometown? Soak up the history of Brooklyn Bridge on a private walking tour of the bridge and Brooklyn neighborhoods. Head for heights? Whizz up the 102 floors to the top of the Empire State Building (think Sleepless in Seattle) then hold hands as you take to the ice (if you start to wobble head to the edges) at The Rink at Rockefeller Center. Or hold hands on the Circle Line, a sightseeing boat tour of the city.

Canoodle as you chew your way through the glorious cooking of NYC, learning the history of Chinatown with a neighbourhood guide. You’ll savor authentic Chinese dumplings as you go. Or how about a two-hour foodie tour of Little Italy, feeding each other slices of pizza, prosciutto and cheese, learning the history and culture at family run bakeries and dairies?

Take your date to a tip to Roosevelt Island on the Roosevelt Island Tram, which is actually a cable car. Coo over aerial views of Manhattan and Queens as you glide on high, following the path of Queensboro Bridge to Roosevelt Island, a slice of land in the East River. Here you’ll be able to take crowd-free riverside walks, enjoy views of the Upper East Side and get stuck into the historical sights the island offers, from North Point Lighthouse to Four Freedoms Park.

If you and your date are open-minded, then stop by the risqué yet deeply informative Museum of Sex (aka MoSex), naturally dedicated to all-things erotic and amorous. Or venture beyond Museum Mile to the Brooklyn Museum, a vast Beaux-Arts building with world-renowned permanent collections from ancient Egyptian masterpieces to contemporary art. Going to the chapel? Spend a few hours at the Met Cloisters, a branch of the Metropolitan Museum of Art dedicated to the art, architecture, and gardens of medieval Europe.It’s a stunning place up in Harlem, which as feels green and tranquil as rural France.

Part mindful experience, part morning rave, jump-start your date with a Daybreaker session you won’t forget (you can opt for less frenetic yoga if you’d rather). Think energising morning workouts with a heavy dose of dance culture and no alcohol, open to all ages. Originally held in venues across Manhattan and Brooklyn, this community project has now ventured into Europe.

The New York Times called it “the Woodstock of eating,” and there’s certainly something hippy-dippy about joining New Yorkers chomping outside. Smorgasburg weekly open-air food market is a buzzy, sociable place for you and your loved one. Wander on down and sample the global flavours of New York – everything from hot dogs to spicy noodles, freshly shucked oyster to stroopwaffels (Dutch waffle cookies). It originated in Williamsburg, in Brooklyn, hence the name, and spread across the city. There’s even one in LA.

Find out why city-meets-country entertainment is all the rage right now in New York at elevated escapes such as Brooklyn Grange Rooftop Farms and the “floating food forest” Swale. The big favorite is the High Line, an elevated stretch of old freight-rail line above the streets north-south on Manhattan’s West Side. With the wild grasses growing and the benches inviting you to sit in sunshine, it’s a romantic way to spend an afternoon into evening, before the first cocktails beckon.

If you get stuck for conversation then elevate the traditional dinner date night to a booking at Syndicated, a cinema-cum-restaurant-cum-bar in the Bushwick neighborhood of Brooklyn screening films and tv shows or the Nitehawk Cinema, independent film showing dine-in venues in Prospect Park and Williamsburg, also in Brooklyn.

Supper Clubs in New York have reached an innovative and quirky status. From clever locations to mouthwatering meals, your date will never forget this cross between a restaurant and an intimate dinner party. At least if you don’t hit it off with your date, you’ll be dining with fellow foodies.

Secondhand shopping is no longer just about finding vintage pieces or quirky garments from a bygone era. It’s also about sustainability and ethical fashion. As most of the profits go directly to charity, show your date you care about the environment and the community. You might just find a bargain birthday gift while you’re browsing. From Greenwich Village to Williamsburg, you won’t be stuck for choice.

Break the ice on a first date with a few laughs at one of the city’s many comedy shows. From improv to open-mic nights, this is a way to find out what makes you both tick, just as long as you don’t get roasted. Humor’s a great way of fast-forwarding your compatibility potential. So go on – be game for a laugh.

This is an updated version of an article originally by Julia Goicochea.