3 Awesome Date Ideas From Start To Finish

They say dating in New York is like playing a game of Risk — or Settlers of Catan, if you want a more au courant reference. While it can sometimes feel like navigating the Arctic tundra, when (not if) you find Mr. or Ms. Right (or Right Now), it all seems well worth the expedition.
So, we put ourselves in singles mode to sort through the wonderland of possibilities that is NYC date planning. Whether you like to be wined and dined or prefer something a bit more adventurous, our mini cheat-sheet of romantic ideas (from start to finish!) has memorable options for everything from a first adventure to a special anniversary. Just don't forget the breath mints…
Educate yourself
I know I'm not alone in thinking the museum is the perfect day-date excursion. Embrace your inner child and head to the American Museum of Natural History for their psychedelic new exhibit "Creatures of Light"—a visual light show of nature's coolest critters. Get goofy and embrace your inner Summer (a la 500 Days of…).
American Museum of Natural History, CPW at 79th Street; 212-769-5100.
Picnic in the Park
Make sure to pack some 30+ SPF (and maybe a thermos of wine) for some fun in the sun in Central Park. Cut through the park and hit up the drool-worthy baked goodies at Le Pain Quotidien, before finding a shady spot in Sheep Meadow. It's the perfect spot for people watching and even more so for a bit of daytime canoodling. (Again, don't forget the breath mints).
Le Pain Quotidien, 2 West 69th Street (between CPW and Columbus Avenue); 646-233-3768.
Hit Up the Highline
Stop into Chelsea Market for some post-sun caffeine pick-me-ups at coffee-fiend favorite Ninth Street Espresso. Stroll through the shops and make your way up to the Chelsea Highline. Grab a bench and cuddle up while you watch the sun set over the Hudson River. It may be cheesy, but it's a site worth seeing.
Chelsea Market, 75 9th Avenue (Between 15th and 16th Streets).
Ninth Street Espresso, 75 9th Avenue (Between 15th and 16th Streets);212-228-2930.
Munch in the Meatpacking District
The Standard Hotel has become the stomping ground for fashion's finest, but it also happens to be a great date destination. Grab a spot on the sprawling patio of The Standard Grill for some speak-easy style cocktails (a proper Ol' Fashioned or anything with Ginger Beer) and a delicious American Bistro style menu. Share a meat and cheese plate or nosh on some of their signature paté's and soak up the Meatpacking magic.
The Standard Grill, 848 Washington Street; 212-64-4100.
Don't be Grumpy
You may recognize this façade from the ever popular HBO saga Girls, but Café Grumpy also serves as one of Greenpoint/Williamsburg's yummiest coffee houses. Grab an iced Americano and nibble on one of their fresh made baked goods—how does PB&J coffee cake sound—before heading off on your Brooklyn adventure.
Café Grumpy, 193 Meserole Avenue (between Newel and Diamond Streets);718-349-7623.
Williamsburg Flea Market
Located right off Kent Avenue, with a perfect view of the East River and Manhattan across the way, the Williamsburg Flea Market is the perfect place to park yourself on a Sunday afternoon. With fantastic vintage finds, cool new crafts and enough delicious food to keep you stuffed for days—please try Asia Dog—this may be the cutest date you'll ever go on.
Williamsburg Flea Market, East River Waterfront (between North 6th & 7th Streets) Sundays from 10am to 5pm.
A Walk in the Park
McCarren Park is the hub of hipsterdom in McCarren Park. With the perfect people watching spots on every corner, lying in the grass is just about the best thing to do on a sunny summer day. Pack a park playlist (might I suggest some Brooklyn-born Cults or Grizzly Bear) and a cozy blanket and snuggle up with some signature take away margaritas from the Turkey's Nest, the somewhat skeezy dive bar across the street. Not that we're condoning public drinking…
Turkey's Nest, 94 Bedford Avenue (corner of Bedford Avenue and N. 11th Street); 718-384-9774.
A Premiere Choice
There's nothing like a good cocktail to finish up the perfect date. Throw back a signature Absinthe concoction at Bedford hotspot Maison Premiere. With the best selection of oysters this side of the bridge, you can slurp back a couple dozen and enjoy the speakeasy vibes of this ultra-charming outpost. And if your date isn't going too well, you can always drool over the dreamy waitstaff.
Maison Premiere, 298 Bedford Avenue (between S. 1st and Grand streets); 347-335-0446.
Strike Out
I personally have a penchant for quirky dates, and there's nothing quite so Zooey Deschanel perfect as an evening spent slamming back some beers and getting your cosmic bowl on. WIth a tummy full of Brooklyn grub, work it off on the bowling lanes at the Brooklyn Bowl. Part concert venue, part bowling alley, you can catch the latest shows while striking out and hopefully getting lucky.
Brooklyn Bowl, 91 Wythe Avenue (between North 11th and North 12th streets);718-963-3369.
Dumpling Date
For those of you with an adventurous palate, Joe's Shanghai, situated in the heart of Chinatown, is the place to be. Inspiring a slew of how-to YouTube videos, you and your main squeeze can giggle over attempting to master consuming their delicious signature soup dumplings. Take my advice; poke, slurp and gobble. You'll understand when you see them.
Joe's Shanghai, 9 Pell Street (between Bowery and Mott Street);212-233-8888.
Gallery Hop
Though Chelsea may be best known for it's onslaught of contemporary galleries, the Lower East Side is quickly catching up. It may take you a bit more time to seek them out, but the upwards of 50 new spaces that have opened up in recent years are housing some of New York's brightest new stars. Try out Jen Bekman Gallery, Show Room or NOoSPHERE for some the latest innovations in the East Coast.
Jen Bekman Gallery, 6 Spring Street (between Bowery and Elizabeth Street);212-219-0166.
Show Room 170, 170 Suffolk Street (between Stanton and E. Houston Streets); 646-559-2856.
NOoSPHERE, 251 East Houston Street (between Essex and Clinton Streets);646-389-8229.
Washington Square Romance
Lucky for us, Bloomberg eased off on the strict bylaws prohibiting busking earlier this year, so Washington Square Park is finally abuzz with the quintessentially New York vibes of the city's best street performers. Grab a couple espressos and some sweet French macarons at nearby Mille-Feuille and bask in the jazz music, break dancing and demonstrations that have followed greats like Mark Twain and Buddy Holly for decades.
Mille-Feuille, 521 Laguardia Pl (between Bleecke and 3rd Streets);212-533-4698.
Laugh Out Loud
New York is home to the origins of great comedy. From the Upright Citizens Brigade to the Pit, famous faces have gotten their starts in the comedy clubs and underground bars for years. Head down to the Comedy Cellar for a few pints and some serious laughs and you might even catch 30 Rock star Judah Friedlander waxing political or former SNL star Darryl Hammond pulling out his signature Bill Clinton. From Louis C.K. to Tracey Morgan, you never know who might show up for a set at this comedy hub. Quick tip: make a reservation here before heading down. Seats fill up fast.
Comedy Cellar, 117 MacDougal Street; 212-254-3480. Weekdays & Sun. 8PM & 10PM; Fri.7, 8:45, 10:30, 12:15; Sat. 7:30, 9:15, 11, 12:45.
Wind Down
Catch the early comedy show so you can take one last trip to the ultra-charming Freemans, located at the end of a quiet alley on the Lower East Side. With an emphasis on home cooking with style and an attractive waitstaff and clientele, this secluded spot has the perfect ambiance for an end of date dining experience—I highly recommend the super-rich but super-tasty Grilled Cheddar Toasts. Cozy up in one of their quiet booths and share a bottle from their impressive wine collection before settling up and setting out for your much-anticipated goodbye kiss.
Freemans Restaurant, located at the end of Freeman Alley off Rivington Street (between Chrystie and Bowery); 212-420-0012.

More from New York