Cure for the Common Date: How and Where to Have Great Dates in Westchester

Listen, we all know first and second dates can be about 13 kinds of awkward. You’re just getting to know each other, the anticipation is through the roof, and the pressure is definitely on to impress the other person. Dinner and a movie? Only if you want to put your date in a coma by the 30-minute mark. Don’t get us wrong—there’s a time and a place for that later in the relationship, once you’re comfortable and situated and have seen each other in sweatpants. But when you’re first starting out, and, you know, conscious, try and think outside the box. Even if the date turns out to be a real dud, at least one of you will have done something you enjoy—and isn’t that what dating is all about?

Fortunately, our area is full of options for all you adventurous, amorous types. Here are a few ideas to get you started. You can thank us on Date #3.

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For the Wild Ones

Westchester Circus Arts Center. photo courtesy of westchester circus arts center

We can think of nothing more thrilling than soaring through the air suspended by a cable—at least, nothing without a significant risk of death or dismemberment. It’s one sure way to find out if you and your date share similar interests. We know the circus probably sounds like a peculiar option, especially if clowns since clowns are, let’s face it, terrifying. Westchester Circus Arts Center ( in Tarrytown, however, offers introductory aerial-skills classes for adults, and that just sounds amazing, right? Get to know your date as you explore different types of aerial skills including working with silks, trapezes, lycras, and rope. Or fall for each other while trying to keep one another upright during the partner balancing classes. Drop-in slots are available for $30 per person, or schedule ahead for a $2 discount. Dates and times vary, so check the website to schedule accordingly.

photo Courtesy of New York Zipline Adventures

For adrenaline junkies, the longest, highest, and fastest zip-line tour in all of North America can be found at New York Zipline Adventure Tours ( in Hunter, New York. It’s also the second largest zip-line in the world. The company offers two three-hour zip-lining options: the Mid-Mountain Tour for $89 per person and the SkyRider Tour for $119 per person. The Mid-Mountain Tour, best for newbies, comprises four rope bridges, a rappel, six zip-lines (the longest measuring 650 feet long and 60 feet above ground) and nine aerial tree platforms. The SkyRider Tour is for the more experienced zip-liner and can reach speeds up to 50 miles per hour over the 4.6-mile-long course. Try not to embarrass yourself by weeping with terror as you soar side by side with your date along five racing zip lines, the first of which is on a 3,200-foot cable at 600 feet above ground.

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Finally, they say the couple that climbs together…er…well, anyway, there are locations all over Westchester that offer open climbs or bouldering, both of which make great date options. Find out just how supportive your potential mate is as he or she belays for you, or test your date’s problem-solving skills as you boulder together. Both The Cliffs ( in Valhalla and The Rock Club ( in New Rochelle offer Climbing 101 classes for beginners, as well as open climb/bouldering sessions for more experienced climbers. Check their websites for hours, class registration, and waivers.

For the (Slightly Twisted) Culture Buffs

The Irrelevant Elephant ( in Mount Kisco offers Date Night: Wine & Painting! every Thursday night from 8:30 to 10 pm. It’s BYOW (bring your own wine), and they have all the supplies for an evening of artistic frivolity. You don’t have to be an artist to enjoy this; just let the wine guide your inner creative genius (some would say it worked for Jackson Pollock), and call it “abstract.” Sessions are only $20 per person.

photo courtesy of the museum of sex

Normally, we’d recommend you stay away from museums for a first or second date. They’re quiet. They’re stuffy. Canoodling too close to the exhibits is frowned upon. Not so at the Museum of Sex ( Located at 27th Street and Fifth Avenue in Manhattan, this museum has exhibits that will fire things up on your date right quick. Admission is $17.50, and the blushing is free. Sure, you might be mortified (or maybe not, you liberated Westchesterite, you) but at least you’ll be mortified together.

Want an excuse to hold hands? How about getting your groove on at Sizzling Salsa, which takes place on Wednesdays at Venue Lounge & Restaurant (venuelounge in Yonkers?  With classes from 6:30 to 8 pm and then dancing from 8 pm to midnight, you can throw nerves aside as you whip around the floor. It’s $15 per person for the full night of classes and dancing, and $5 without the class (if you decide you’re good enough). All skill levels are welcome, so don’t worry about making a fool of yourself. And if you do, so what? Mutual embarrassment can be a bonding experience.

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For the “Foodies”

First, never describe yourself as a “foodie” unless you truly are one. The temptation is strong to impress at all costs, but unless you’re Boulud’s secret protégé, you’re risking an embarrassing revelation the first time you spray cheese from a can onto a cracker in front of your date.

This is all about trying new things, so instead of regaling your date with that story about the time you made a delightful roulade, why not take a class and actually learn a little something about food and drink—together? The Astor Center (, located in NoHo, Manhattan, offers cooking and cocktail classes with tantalizing options like No Goat Left Behind with momofuku’s Matthew Rudofker; Aw Shucks: A Hands-On Oyster Primer; and Whisky Smackdown: Scotch vs. Bourbon. Classes are perfectly timed for a date at around two to three hours, and nothing says romance like the severed shells of a bivalve.

For the Attention Hogs

Karaoke is almost more fun to be bad at. At least, that’s what we tell ourselves halfway through “Rock You Like a Hurricane.” Why not break the ice by belting out a favorite tune and cheering on your date while he or she does the same? Even if you can’t work up the nerve to give it a whirl, you can mock the tone-deaf together. Audition for White Plains Idol at Vintage Lounge & Restaurant ( in White Plains every Thursday night starting at 8 pm.

For the (Sort of) High Rollers

Manhattan by Sail

Impress your date with a trip around New York City in your private yacht. What? You don’t have one? Well, in that case, try a Champagne brunch and a sail aboard the Shearwater, a Newport-style schooner (and  National Historic Place) built in 1929 and operated by Manhattan by Sail (manhattanby The two-hour Champagne Brunch Sail departs North Cove Marina in Lower Manhattan at 11 am on Sunday mornings and offers a generous selection of brunch options and unlimited Prosecco from the Champagne bar for $95 per person. You can sit inside or outside, or even help the crew sail the ship if you have the skills to do so.

For the (Actual) High Rollers

Wings Air

It’s a bit of a splurge, but worth every penny, to take a private helicopter tour over New York City. Wings Air (wings, located at the Westchester County Airport, offers private 30-minute tours for $995 (for up to six people, if you opt to make it a group date).  If that’s a bit rich for your blood, then you can do a group tour for $200 per person. (Be sure to stalk Groupo for deals on group tours.) Nothing says romance like an aerial view of the City and the historic Hudson Valley at sunset. Just a suggestion: Discuss how you are going to pay for this before you get there. And, ladies, don’t reach for your wallet if you don’t intend to pay. That can go all kinds of wrong and backfire on you.

Whatever activity you choose, just be comfortable in your own skin. You’ve already secured your date, so be the person he or she was attracted to in the first place. Loosen up, and don’t be afraid to step out of your comfort zone. We promise, it’s not that scary. Unless, of course, there are clowns.


Cat Zambito, aside from being a freelance writer, also works as a voice-over artist and actress in Manhattan. She lives with her husband and son in Mamaroneck.

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