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Great second-date ideas in NYC: Where to have a fun second date

Now that you feel more comfortable, plan a more involved outing at these great spots for a second date in NYC.

 (Photograph: Filip Wolak)
Photograph: Filip Wolak

The Stand


Molasses Books

 (Photograph: Mathilde Roussel Giraudy)
Photograph: Mathilde Roussel Giraudy

French Institute Alliance Française


Fatta Cuckoo


 (Photograph: Donald Yip)
Photograph: Donald Yip

The Queens Kickshaw

Once you get past first-date awkwardness, planning a second date can actually be kind of fun. Use these great second-date ideas to craft a fun outing: Get to know each other by looking through the shelves at Molasses Books, or plan a classy outing at the French Institute Alliance Française’s free First Tuesdays.

RECOMMENDED: More great dates in NYC 2013

Giggle (and pig out) at the Stand


If you ended the first date swapping lines from your favorite episodes of Mr. Show, keep the comedy-nerd sparks going at this new club. The lack of a drink minimum at the tables is as refreshing as the signature cocktails, which include the Boozler ($13), a combination of Ransom Old Tom gin, tarragon, ginger liqueur and pear puree. Snack on small plates, such as Tater-Tot nachos ($13), while watching local comics, such as Judah Friedlander, Janeane Garofalo and Wyatt Cenac.

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Share your shelf recommendations at Molasses Books

Afternoon dates are ideal: You can make it clear that you’re into more than hooking up and remember your conversation the next morning. Turn browsing into an all-day activity at this new Bushwick indie shop, whose trade-in program allows you to swap used books for store credit (which you can spend for more books or at the café). The informal space is ideal for disarming the pretension that comes with comparing favorite novels. Use your credit to grab a couple cans of Genesee cream ale ($3/can), then hunker down and stay a while. facebook.com/molassesbooks

Class it up during FIAF First Tuesdays


Show that you’re a sophisticated, suave mate (even if you’re totally not) by suggesting an outing to the French Institute Alliance Française’s free open house. On the first Tuesday of the month (6–8:30pm), the cultural institution opens its doors—and uncorks the wine—for Francophiles, relieving you of the itinerary-planning pressure. Learn to say hot-sounding phrases during an instructor-led beginner French lesson, then grab a glass of vin in Le Skyroom, an eighth-floor event space with floor-to-ceiling windows overlooking midtown Manhattan.

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Upper East Side

Go for drunk brunch and visit an artsy Soho spot

Don’t get stuck making nervous conversation while you wait an hour for brunch: Book reservations for drunch—drunk brunch—at Fatta Cuckoo (63 Clinton St between Rivington and Stanton Sts; 212-353-0570, fattacuckoo.com). For $25, you’ll get an entrée—try the classic bacon, egg and cheese sandwich—and three cocktails, like a Red Snapper (a Bloody Mary riff made with gin). Thus fortified (and slightly inebriated), wander through downtown before stopping by the newly opened Leica Store New York Soho (460 West Broadway between W Houston and Prince Sts, 212-475-7799), which, along with its famous cameras, features rotating photography exhibitions. (The current show spotlights the work of Danish photographer Jacob Aue Sobol.)

Nosh on comfort food at Queens Kickshaw

Dinner may be a second-date standby, but that doesn’t mean planning it is a no-brainer. The right spot should combine cool and casual, with plenty of menu options and a moderate price range making it easy to go dutch. Astoria favorite the Queens Kickshaw fits the bill with can’t-miss comfort foods (try the classic grilled-cheese-and-tomato-soup combo, $8), plus an extensive—and inexpensive—wine and beer list. Head there on a Friday night, when live music from local bands will help cover any awkward silences.

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