I'm what you called a "serial dater." And, thanks to my experience in the dating realm, I've perfected not just the art of the awkward and intimidating first date, but those "Where is this relationship going?" meetings that follow, as well. Oftentimes we're so consumed by the first date, that we forget that second dates are an even higher-stakes game — you've made a good enough impression for a person to call again, but will this lead to more?
After the initial nerves of the first date wear off, second dates can actually be more of a thrill. They're also a lot more fun to plan. You've learned the barebones of your partners interests and have the ability to play to them in one magical night. It sets the tone, in ways, for the kind of relationship you might envision with that person — who knows, maybe that late-night karaoke session will end up being
the date the two of you recall to your friends as the moment you knew you were head over heels for each other.
Of course, some of the best dates happen in the weirdest of circumstances, or with no real plans at all (True story: The best date I've had in New York was a stroll down Super Bowl Avenue in Times Square accompanied by late-night games at Dave & Buster's). But, after a while, I inevitably fall back on my list of my spots guaranteed for a good time (No, not that kind of a good time). A second-date spot should be comfortable, adventurous, and out-of-the-box enough to keep them intrigued — and with these
ideas, they’ll without a doubt be wondering by the end of the night just what else you might have up your sleeve.
Photo: Getty Images.
For The Star-Gazer: The High Line
Every Tuesday night between April and October, the Amateur Astronomers Association of New York heads to the High Line with their powerful telescopes to help passers-by gaze at stars, planets, and other out-of-this-world sights. Even if you know nothing about space, getting a close-up view of Jupiter is sure to impress your date.
The Diller-von Furstenberg Sundeck
, on the High Line at 14th St.
Photo: Eye Ubiquitous/UIG/Getty Images.
For The Kid-At-Heart: Jane's Carousel
Jane's Carousel is more than just a ride for kids (and adults) — it's practically a work of art. It was created in 1922 and boasts 48 intricately carved horses and two chariots. Better yet, the carousel sits underneath the Brooklyn Bridge and in
close proximity to plenty of restaurants
, a gorgeous waterfront, and one delicious ice cream shack. It's just the kind of romantic setting that could lead to date number three.
, Brooklyn Bridge Park (between the Brooklyn and Manhattan bridges).
Photo: Volkan Furuncu/Anadolu Agency/Getty Images.
For The Nature Lover: Brooklyn Botanic Garden
What's more romantic than wandering around a beautiful, flower-filled garden? Unfortunately, nature is hard to come by in New York City, and that's what makes places like the Brooklyn Botanic Garden even more special. Besides, a long walk among the plants leaves plenty of time to really get to know your potential new love.
Brooklyn Botanic Garden
, Entrances at 455 Flatbush Avenue, 150 Eastern Parkway, and 990 Washington Avenue.
Photo: Joshua Lott/Getty Images.
For The Nostalgic Gamer: Barcade
Remember all of those video games you loved in the '80s and '90s? Pac-man, Donkey Kong, Frogger, Tetris — Barcade has them all. This is the perfect place for you and your date to relive your childhood, with the added bonus of an extensive beer selection.
, 6 St. Marks Place (between 7th and 8th streets).
Photo: Courtesy of The Commodore.
For The Low-Key Date: The Commodore A general rule for singles to live by: If you can't like someone over cheap beers, comfort food, and jukebox music, you won't like them any more over a three-course dinner. Finding that perfect compromise between $2-PBR dive bar and overkill fancy-beer bar is tough, though; that's why we like The Commodore so much. It's got the best cheap bar food in Brooklyn, kitschy cocktails (like house piña coladas and hurricanes), and old arcade games, in a space that doesn't feel like a dive. The Commodore, 366 Metropolitan Avenue (at Hope Street); 718-218-7632.
Photo: Melody Ann Crespo/Flushing Meadows Corona Park.
For The Outdoors Enthusiast: Flushing Meadows Corona Park
Central Park and Prospect Park are so passé. A quick trip on the 7 train sends you straight to the city's most underrated green space. Flushing Meadows Corona Park was home to the World Fair 50 years ago, so you'll see the gigantic globe that was erected just for the occasion (You can also peek into the Queens Museum for more galleries on the World Fair, as well as a massive pop-up diorama of the five boroughs). Bike the greenways or stroll down the promenade when it's warm, or lace up your ice skates for some winter fun — the park is big enough for all of your outdoor adventures.
Flushing Meadows Corona Park
, Grand Central Parkway (Whitestone Expressway between 111th Street and College Point Boulevard); 718-760-6565.
Photo: Noah Fecks/Bar Primi.
For Those Lacking The Second Date Jitters: Bar Primi
You've officially made it: Your date has suggested you have dinner for a second time, and you're clueless as to where to go. We've got you covered, and it's a recently opened Italian restaurant they probably haven't been to yet. Bar Primi, the latest from chef Andrew Carmellini, is stocked with simple-yet-elegant pastas (because love happens over red wine and lots of carbs), appetizers, and meats. It's casual enough to feel unpretentious, but packed with the romance and charm of an Italian eatery.
, 325 Bowery (at East Second Street); 212-220-9100.
Photo: Daniel Ramirez/Brooklyn Bowl.
For The One Who Likes To Get Playful: Bowling at Brooklyn Bowl
Nothing brings out the mischievous, competitive side of someone than some good ol’ fashioned games. Brooklyn Bowl is the perfect icebreaker to get silly, cheer each other on, and down some Brooklyn Brewery suds. Loser buys the next pitcher of beer, or better yet, owes the winner a kiss. Keep the fun going with some Blue Ribbon chicken after the game.
; 61 Wythe Avenue (between 11th and 12th streets); 718-963-3369.
Photo: Courtesy of Strand Book Store.
For The Nerd: Strand Book Store
Another New York institution that makes you feel straight out of a rom-com, the Strand offers more than enough chances to get lost among the stacks. There's something settling about gabbing (quietly!) while perusing the shelves for the next must-read. And, while you may find a couple of armchairs here and there to converse in, instead take your purchases up the street to Max Brenner to chat over hot chocolate, or just east, to Everyman Espresso.
Strand Book Store
, 828 Broadway (at East 12th Street); 212-473-1452.
Photo: Courtesy of Dead Rabbit.
For The Cocktail Aficionado: Dead Rabbit
Anyone following the bar scene in New York will be impressed that you suggested the "the world’s best cocktail bar," two years running, for drinks. Dead Rabbit perfectly contains all you need for a great date: A sophisticated-yet-comfortable bar area with lots of booths for close quarters, killer cocktails (like the Wild Irish Rose, pictured here), and a relaxed pub area downstairs for grabbing that post-date burger.
, 30 Water Street (between Broad Street and Hanover Square); 646-422-7906.
Photo: Lauren Wohl/Gallow Green.
For The One You Fell For Immediately: Gallow Green at the McKittrick Hotel
For such a swoon-worthy city, few bars top Gallow Green for a place of romance in New York. Riding up the elevator to the rooftop (it's located at the top of the McKittrick Hotel, home to
Sleep No More
), you'll feel transported to a twinkly lit, lush green forest overlooking the Hudson River. Late weekend nights can bring out a party-hard city crowd, but drinks under the canopy give way to butterflies and kisses under the stars.
Gallow Green at the McKittrick Hotel
, 542 West 27th Street (between 10th and 11th avenues); 212-564-1662.
Photo: Daniel Krieger/Gotham West.
For The Ultimate Foodie: Gotham West Market
Gotham West Market is a food lover's dream, and the market gives you the perfect opportunity to geek out about your favorite dishes. It's a low-key way to get to know each other's tastes — is your date an Ivan Ramen fanatic? A meats-and-cheese kind of person? A coffee snob? Go ahead and pick your poison — and while you still can (through the end of September), grab a Jeni's ice cream cone and head to Pier 84 to catch the sunset.
Gotham West Market
, 600 West 11th Avenue (between 44th and 45th streets); 212-582-7940.
Photo: Courtesy of Casa Mezcal.
For The Wine and Spirits Lover: Casa Mezcal
Your date may consider themselves to be somewhat of a bourbon fiend — or maybe a fine-wine appreciator — but is there a sexier drink than tequila? (There's a reason they say tequila makes your clothes fall off.) Casa Mezcal serves up a side of sultry spirits in a Oaxacan three-story restaurant, bar, and performance space. Conduct your own tequila or mezcal tasting, or sip on one of the bar's classic cocktails. Who knows, maybe the liquid courage will encourage an exploration of a platter of mole de pollo.
, 86 Orchard Street (between Broome and Grand streets); 212-777-2600.
Photo: Courtesy of Hill Country.
For The Seriously Outgoing Individual: Live Band Karaoke at Hill Country Barbecue
Few spots in New York offer karaoke with as much gusto as Hill Country Barbecue in Flatiron. The "Rock 'n' Twang" event on Tuesday nights brings out the live-band backup for all of your show-stopping numbers — and what better way to charm your date than with your musical talents and/or boldness. If the bourbon doesn't offer you both the liquid courage to get up on stage, we guarantee you'll still get quite a show (trust us, we've seen
Hill Country Barbecue
, 30 West 26th Street (between Sixth Avenue and Broadway); 212-255-4544.
Photo: Courtesy of Marco's.
For The One Who Takes Brunch Seriously: Marco's
We love a good dinner date, but a good
date is kind of a no-pressure way to get to know someone. Marco's takes your beloved boozy brunch and elevates it to a more refined level. Think wood-grilled oysters, whole-wheat chocolate doughnuts, grilled zucchini cake with gelato made at neighboring BKLYN Larder, Campari sours,
Italian sparkling wines at this cozy trattoria. Stay for awhile — this is the kind of brunch date you'll want to settle into.
, 295 Flatbush Avenue (between St. Marks Avenue and Prospect Place); 718-230-0427.
Photo: Courtesy of Cafeteria.
For Those Who Don't Want The Date To End: Late-Night Diners
The easiest way to prolong any date that's going well? A pancake breakfast at 1 a.m. Any greasy spoon will do when the two of you just can't stop talking, but we've had our best diner dates in Chelsea. You'll find anything from hole-in-the-wall Johny's Luncheonette to fancier spots, like Cafeteria and Empire Diner.
, 124 West 25th Street (between Sixth and Seventh avenues); 212-243-6230;
, 119 Seventh Avenue (between 17th and 18th streets); 212-414-1717;
, 210 Tenth Avenue (between 22nd and 23rd streets); 212-596-7523.
Photo: Sebastiaan Ter Burg/Smalls Jazz Club.
For The Cultural Maven: Live Jazz in the West Village
The classic New York date doesn't occur on the top of the Empire State Building, as romance films might tell us — they happen wandering the streets of the West Village, looking for dark and sexy clubs to sneak into for cocktails and tunes. And, there's plenty of clubs on the west side to get your dose of old New York culture. Places like Village Vanguard charge an arm and a leg for tickets and have drink minimums, so we like making our own jazz crawl. Take a stroll up and down Seventh Avenue and pop into some of our favorite bars with live music and low cover charges, like the
Smalls Jazz Club
. If you find yourselves jazzed out by the end, make a final stop at Fat Cat for a casual game of shuffleboard, cheap beers, and live music.
, 75 Christopher Street (between Bleecker Street and Seventh Avenue South); 212-675-6056.
Photo: Courtesy of La Tacqueria Kermes.
For The One Ready For An Adventure: Tacos in Ridgewood Anyone who's willing to break out of the typical New York neighborhoods for a date allows for all kinds of out-of-the-box ideas. Prepare for an NYC kind of adventure by heading to the outer boroughs in search of the best tacos (because let's face it, anyone who doesn't like tacos probably isn't worth your time). Bring your own six-pack to La Taqueria Kermes for some mind-blowing surf-and-turf tacos, or go all-out hidden gem at Fresh Pond Mexican Restaurant. End the date by popping into any no-name dive bar on Fresh Pond Road, too — you won’t want this mini food quest to end. La Tacqueria Kermes, 66-36 Fresh Pond Road (between Woodbine and Palmetto streets); 349-463-9263; Fresh Pond Mexican Restaurant, 67-22 Fresh Pond Road (between 70th and 71st avenues); 718-366-1595.
Photo: Courtesy of Proletariat.
For The Beer-Lover: Proletariat
So, your date drops the bomb that they're a beer nerd — and by nerd, we mean connoisseur to the nth degree. Proletariat promises all the unusual, hard-to-find beer gems you won't find on just any menu. Tuck yourselves into the back corner of the bar (make sure to arrive early to get a good spot, as it gets busy on weekend nights), and treat yourself to a one-of-a-kind beer tasting. A craft-beer drinker yourself? You’ll have plenty of opportunities to demonstrate your knowledge about rare saisons and barrel-aged porters. New to craft beer? Let your date talk you through the beer while snuggling up.
, 102 St. Marks Place (between First Avenue and Avenue A).
Photo: Jonathan Mcintosh/Sweet Revenge.
For The Sweet Tooth: Cupcakes at Sweet Revenge
Sweet Revenge's line of artisan cupcakes are sinfully delicious, and its full wine and beer list only sweetens the deal. Grab the front counter to gaze out the window (it's a teeny space, so we recommend getting there before or after the dinner rush) while the two of you split some dessert with one of the suggested drink pairings. It's just the right amount of casual-yet-romantic to fall hard — and debate a second serving of frosting.
, 62 Carmine Street (between Leroy and West Houston streets), 212-242-2240.