No matter how well you two know one another -- whether it’s your first Tinder date or you’ve made it to the one-month mark -- the city is full of ways to actually have fun on an early-in-the-game date.
But don’t make it harder than it has to be by subjecting your date -- and yourself -- to a painfully ordinary night of dinner and drinks.
Alamo Drafthouse has super-comfortable seating (reserve seats in the first row if it's that kind of date and you want to recline) and a lengthy menu of dishes like pancetta mac & cheese and jerk chicken sandwiches.
Save room for one of the throwback shakes or floats.
Take the ferry across the Hudson to Jersey City for a full-on day trip.
On a first date, it's vital to have available distractions should the banter come to an agonizing halt.
Warm-weather second dates are best spent on Governors Island.
Bring or rent bikes to enjoy the expansive network of cycling trails, plan your trip around a special event (like the annual interactive FIGMENT art installation or the Jazz Age Lawn Party), or check out the new zip-line course.
From there, it's only a 15-minute walk to Flushing Meadows Corona Park: the site of two 20th-century World's Fairs.
There's something decidedly eerie about the Tent of Tomorrow and Observation Towers, but the Unisphere globe, commissioned for the 1964 fair, is the perfect backdrop for your first selfie together.
If you're looking for great music with your second-date drinks, hit up Shrine, Harlem's bodega-meets-world-music venue, which offers $3 draft beers during happy hour with live music. Once a month at The Bedford, the Society for the Advancement of Social Studies hosts hilarious (and totally free) lectures on a wide range of bizarre topics like German sabotage in New York City during World War I or an ill-fated American history theme park in the Bronx. You don't need to be staying at a hotel for access to the rooftop pool -- you can easily pay for a $40 day pass to La Piscine at Hotel Americano or $65 for The Beach at the Dream Hotel (among others) and pretend you're miles away from Manhattan.