At Thrillist, we pride ourselves on being decent, law-abiding citizens, who would never dream of engaging in illicit activities. However, we know you, our readers, are deliciously filthy degenerates who crave the opportunity to spice up your dating lives with a brush with the felonious. Of course, we don’t recommend actually trying any of these illegal NYC date ideas below, no matter how delightful, romantic, or adrenaline-inducing... we’re just... going to leave them here.
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Hit the bar, then sneak into the bathroom and paw each other’s clothes off
How to pull it off: We’ve offered you a guide to public-bathroom sex before, but here are some specific tips: the bathroom at The Woods in Williamsburg is basically made for a quickie. We do mean quick, though -- don’t let that line form. Of course, if grime and exhibitionism are more your speed, the Double Down Saloon in the East Village has a giant hole in the wall between their two bathrooms, so if you’re in the mood, you can put on a show. Laws you’d be breaking: Public lewdness, plus the most important, unwritten law of God and man: the one that forbids holding up a crowded bathroom line full of people who have been drinking
Shoplift a pair of plastic animal masks from a dollar store, then wear them down the street
How to pull it off: Walk slowly, keep your head down, avoid turning your face toward store employees, calmly exit the shop, then race down the street giggling. Watch the most charming scene in Breakfast at Tiffany’s on repeat for further tips. Laws you’d be breaking: This one is a surprising double whammy: while it’s kind of obvious that you might get busted for shoplifting, it’s also actually illegal to wear a mask in a public place in New York.
Sneak into a fancy event and steal some canapes and cocktails
How to pull it off: Find a large, swanky, brand-sponsored event, hand a high-quality camera to your date, and bring your acting A-game. Try addressing the public-relations rep in an incredibly friendly manner and cite the name of your made-up blog. Be baffled that you’re not on the list. Gesture to your date, who should stay silent and look bored out of their skull, and plead, “But I brought our photographer!” Chances are they’d rather let you in than miss out on some potential coverage -- this works especially well during fashion week. Laws you’d be breaking: You’re either going to get in the door or not, but technically, you could end up getting slapped with trespassing and theft.
Start a dance party any place that isn’t a licensed cabaret
How to pull it off: Hit up any dive bar with a solid jukebox and bust some moves; as soon as three or more people are getting their groove on, dancing without a license is technically illegal. The best part of this one is that it’s incredibly unlikely that you’ll get caught, but you and your date can secretly smile to each other, secure in the knowledge that you just generated a Footloose-style stand against the man. Laws you’d be breaking: This totally absurd law from the 1920s that is very selectively enforced
Drink a bottle of wine on Brooklyn’s industrial waterfront
How to pull it off: Dark clothes, good climbing shoes, whispering, and maybe bolt cutters, depending on how serious you want to get. Wait until it’s nice and dark, then find a way into any of the piers and rocky spots along the East River off Kent St north of West 10th, or anything east of West St. In order to not get nabbed for drinking, conceal the wine. Here’s our twisted “Hints from Heloise” for the day: a standard 750mL bottle of cab pours neatly into a 24oz POM Wonderful bottle, with just an ounce and a half left for swigging. Laws you’d be breaking: Trespassing, for sure, but maybe also breaking and entering, flexing with open-container laws, and potentially being intoxicated in public (depending on how much of a lightweight you are)
Grab swimsuits and hit up one of New York’s several swanky hotel pools
How to pull it off: We’ve already given you the guide on how to sneak into plenty of pools in New York, but here are the basics: dress like you belong there; take long, purposeful strides; be gracious to hotel staff (“Oh, we left our key upstairs -- thank you so much”); and if all else fails, charm some guests into swiping you in. Laws you’d be breaking: Breaking and entering, trespassing, and that unwritten law against partaking in activities that are so cute they’re more likely to occur in a rom-com than real life...
Explore Green-Wood Cemetery after hours
How to pull it off: The cemetery closes at 5pm, so you have some options here: if you’re up for a long night, you can just get there at 4:45 and hang out until everyone has gone home. Alternatively, hop a fence or even climb the gates (they’re not impossible). Of course, some of the fences are topped with razor wire, so... you know, don’t choose those. Laws you’d be breaking: Breaking and entering, trespassing, etc., etc.
Check out the 1964 World’s Fair New York State Pavilion in Queens
How to pull it off: Bring bolt cutters, and be prepared to snip up the bottom of some chain-link fence, as well as some locks and chains. We genuinely don’t recommend climbing this thing (it’s way dangerous), but wandering around the base is totally worth the effort -- not that you should do it. If you want to check out the inside, there’s a door in the tower, but you’d have to bring the capacity to snip through a lock or two. Laws you’d be breaking: Oh, you know, the usual: breaking and entering, aggravated trespassing, willful destruction of property...
How to pull it off: Fort Tilden beach in Queens is one of the more secluded locales for this activity, which makes this a little easier to pull off. The closest parking is Jacob Riis (where skinny dipping is also known to go down after the lifeguards head home). But if you’re trying to strip down during daylight hours, it’s worth the extra hike. Laws you’d be breaking: If anyone sees you and gives a damn, you could get slapped for indecent exposure.
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Jess Novak is so law-abiding that she makes citizen's arrests as her primary form of entertainment. Follow her unerringly pristine antics on Twitter @jesstothenovak and Instagram @jtothenovak.