As exciting as dating can sound on paper (Meeting new people! Maybe seeing someone naked!), the reality is that dating can kind of suck. It can be a frustrating and tedious experience, and realistically, how many coffee dates or dinners can you fill your dance card with before total boredom sets in? Instead of yet another yawn-inducing night out, impress your date with something a little more interesting (and uh, possibly illegal). Not that we’d ever suggest anyone be anything BUT a law-abiding citizen... but if we did, here are 9 illegal date ideas in Toronto that could make your dating life a lot more exciting. Or get you arrested. Now that's a story to tell your grandkids!
Go for a midnight swim at one of Toronto’s public pools
How to pull it off: Sure, Toronto bylaws state that no person can enter a public swimming pool except at designated swimming hours, but where’s the fun in that? Wear your best fence-hopping pants because you’re going to need them. Give your date a boost (or get one from your date), discreetly make your way over the fence, try and land quietly, and then dive in. Bonus (illegal) points for making this a skinny dip.
What laws you’d be breaking: Some light trespassing, breaking and entering, indecent exposure if you opted out of swimwear. Plus, swimming where and when you’re not supposed to be.
Skinny dip at the beach
How to pull it off: Hanlan’s Point Beach is the only place you can legally bare your naughty bits while swimming in the city, but that doesn’t mean you should relegate your skinny dipping to one measly stretch of sand. Toronto beaches tend to get crowded, but you might be able to find a secluded spot if you make this a weekday date, ideally early in the morning or late at night.
Laws you’d be breaking: Indecent exposure, some possibly unfortunate shrinkage.
Con your way onto the roof of the Thompson Hotel
How to pull it off: Toronto has some pretty swank hotel pools, but not many of them allow anyone except guests to enjoy them. One of these is the gorgeous rooftop pool at the glitzy Thompson Hotel. Your best bet is looking like you belong, dressing the part, and acting bored with the whole thing (sure, I guess I’ll go to the pool if there’s nothing else to do). Failing that, see if you can convince someone who actually belongs there to swipe you in.
Laws you’d be breaking: Breaking and entering, trespassing, etc.
Have a boozy picnic in Trinity Bellwoods Park
How to pull it off: Aside from a picnic basket filled with an impressive array of handheld snacks, all you need for this one is the ability to drink discreetly and a smart way to conceal your booze. Decanting wine into solid reusable water bottles won’t do much for aeration, but it will allow you enjoy a nice glass of pinot with your picnic.
Laws you’d be breaking: That silly one that says drinking in parks is illegal.
Sneak into a fancy event
How to pull it off: We’ve all seen those events, the sleek and stylish ones where someone important-looking is holding a clipboard, taking names, and deciding who can come in and who gets relegated to the sidewalk. The thing with these events is that the food is usually great and the booze is even better. Sometimes, you can even nab a stocked gift bag when you leave. Dress in your finest, walk like you mean it, and when you get to the clipboard-wielding woman with the headset, haughtily swear up and down that your name should be on the list, throwing in a vague threat or two about 'somebody getting fired for this.'
Laws you’d be breaking: Trespassing, eating food that isn’t yours, identity theft (or something).
Set up a lemonade stand in a public park
How to pull it off: Why not attempt to make a little extra coin on your date by setting up a stand and selling refreshments? This one is tricky because you’ll want to set up somewhere with a lot of foot traffic if you want to actually turn a profit, but that puts you at risk of exposure. To the cops. Ah well, no risk, no reward, am I right? Not that we’re condoning it...
Laws you’d be breaking: Illegally offering delicious beverages to fellow park-goers. In Toronto parks, unless authorized by permit, you can’t sell, offer, or display for sale any food, drink, or refreshment.
Have sexy times in a tent at the park
How to pull it off: What’s better than getting frisky outdoors? Unfortunately, even an attempt to be discreet about your forest-frolicking can lead to a fine, but if excitement and owing money to the government are turn-ons, have at it. Find a low-key spot to set up a tent in the park, put up a 'do not disturb' sign, and get to taking each other's pants off.
Laws you’d be breaking: Unless you have a permit, setting up that tent is a no-go in the city’s public parks. Plus, there’s also that weird, illegal thing about sex in public places.
How to pull it off: Basically, this just involves a lot of cojones and the god-given ability run really fast. Find an area that speaks to your streaking side, disrobe, and go for a run. The adrenaline this act generates will ideally translate to some rambunctious sex later in the date. But don’t do any super-public sex-type things in the park because then you’d be breaking a bunch more laws and we truly can’t condone that.
Laws you’d be breaking: Sadly, Toronto bylaws state that while in a park, no person shall be nude. Bummer.
Sneak into the movies, bring booze
How to pull it off: OK, movies are a conventional date, but you can spice things up by skipping the ticket counter and sneaking in some hooch. Stride in, plastic bottles filled with booze in tow, sneak past the guy taking tickets, or if he notices, frantically pat your pockets while saying nervously that you can't find your stub!!!! (There is no shame in a fake tear or two.) Sympathy and free passage acquired, head to the show of your choice and make out in between swigs of your bootlegged drinks in the last row of the theatre.
Laws you’d be breaking: Breaking and entering, annoying other patrons with your heavy petting, something about open container laws.
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Jessica Padykula is a (mostly) law-abiding citizen who doesn't even jaywalk, but she may have done at least one of the things on this list. She's just not telling you which ones. Follow her on Twitter and Instagram @JessPadykula