All of my first and second dates in New York City have gone exactly like this: meet date, drink across from or next to or in general vicinity of date at the most convenient (to me) bar, leave, lose hope in finding another human to enjoy the next week or forever with. In my head—and heart—however, all I want is the kind of date that Hollywood has manipulated me into believing can exist. One with unplanned and seemingly imperfect but actually perfect moments, casual and witty banter... pretty much any scene between Ryan O'Neal and Ali MacGraw in Love Story. (Even the death one!) I am certain that people are having these idyllic date moments all around me, all of the time.
The below list is what I believe would be the perfect second date—where you're a little familiar with the person already—as has been dictated to me through years of watching rom-coms. The key, you'll see, is not overcomplicating and overplanning it.
A Museum: Most museums in the city offer a First Friday, but the best one is First Friday At The Frick. The first Friday of every month the Frick hosts a free evening, where you can roam around and view the current exhibit and permanent works. The bonus, however, is that the Frick has a gorgeous atrium, where you can grab a bench, listen to the live classical music, enjoy some light snacks (note: there's no alcohol), and do some drawing (the museum provides stools and sketching materials!). There are also talks throughout the night that you could hop in and out of. If things go well, maybe head over to nearby Central Park after! Tip: Get there early (around 5 p.m.) to avoid too long a line.
The Frick is located at 1 E 70th St (at 5th Ave) on the UES
A Pocket Park: The city has some wonderful pocket parks, and if you're looking for a quiet oasis to get to know your date, head over to one of those, even to just start off the evening. Pictured above is Greenacre Park, one of the loveliest places in all of Midtown to be sure, where you can even grab some ice cream or just take your first selfie together [eye roll emoji] in front of the waterfall. Here's a list of some our favorite pocket parks — find one near you, and check the hours before you go.
Pocket parks are located all over the goddamn place, you just need to know where to look
A Carousel: The city has some lovely carousels, both new and historic, and they're perfect for a casual date. In Battery Park you'll find the mesmerizing LED-lit SeaGlass Carousel (which stays open until 10 p.m. and only costs $5). There's also the circa 1922 Jane's Carousel in Brooklyn Bridge Park (open until 7 p.m., and costs 2 bucks). The bonus with that one is you can watch the sunset over the skyline afterwards.
You'll find carousels in Manhattan, Queens, Brooklyn, The Bronx, and Staten Island — here's a fairly comprehensive list.
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A Quiet Bar: Not every bar works—depending on the hours and location, you could find yourself amidst 100 bros donning RompHims. Gothamist's Ben Yakas informs me that a good lowkey second date spot can always be found at a local bar, dive or fancy, and his favorite is Angel's Share "on a Monday or Tuesday night, when they are less busy. The best cocktails I've had, romantic dimly-lit setting, and many of the cocktails are named after jazz songs/artists." If you sit at the bar, you can watch them create their impeccable cocktail masterpieces before you imbibe.
Angel's Share is located at 8 Stuyvesant St, near 3rd Ave
The Ferry: Former Mayor Michael "Regular Guy" Bloomberg once claimed that the Staten Island Ferry was the most romantic place in the city, or at least it's a good date spot. You can brown bag some booze, sit back, and take in the skyline from the bright orange vessel. (They also sell beer on board.) It's the city's own Tunnel of Love, albeit open-air. And comedian Todd Barry agrees—he told us, "The Staten Island Ferry is a great idea for a date, as long as that ferry is headed to STATEN ISLAND’S HOTTEST SMALL PLATES RESTAURANT!" Literally no one knows romance like Bloomberg and Barry, so take their words for it.
The SI Ferry, which is free, runs between the Whitehall Street terminal in Lower Manhattan and the St. George ferry terminal on Staten Island. It's free.
N.B.: Most of the above can be taken to the next level with a little special surprise: a flower, a flask, a little token calling back to something you learned about the person on your first date. Be creative, but also be casual... this is only the second date, after all.