We don't exactly have to remind you that dating can be a total drag. No two people who agree to go out with each other want to yell lines of small talk over the music and chatter of a loud bar while fielding "it's a Tinder date" glances from everyone around you. Maybe it's time to mix it up with something, perhaps, a little riskier? Not that we'd ever encourage you to do anything illegal, like the date ideas below...
Watch the sunrise from Silo 5
How to pull it off: Reaching the roof of this abandoned grain-processing building is easier said than done. The place is fairly well patrolled by its own security, and the best way to avoid getting caught is to go at 4 or 5 in the morning. The trek to the top takes about 30-45 minutes and includes some fence hopping and leaps over watery ravines. Once you get to the top, however, you’ll be exposed to one of the most impressive sunrise views of Montreal you could possibly imagine. It doesn’t get more romantic than that.
Laws you’re breaking: Trespassing
Take a midnight stroll in the Notre-Dame-des-Neiges Cemetery
How to pull it off: You should go the cemetery on Chemin de la Côte-des-Neiges at night. It’s pretty simple. Just make sure to avoid any sort of police or security, because you certainly can’t be in there after it closes. If, by chance, your date is sadistic weirdo, then they’ll absolutely love this romantic romp through the graves. At almost 345 acres, it’s actually Montreal’s biggest cemetery, so you’ll have plenty of ground to cover.
Laws you’re breaking: This is a tricky one due to something called "sanctuary." Essentially, you’re breaking the law by trespassing in the cemetery. If you have no dead relatives buried there, then you’re out of luck. But! If you actually have someone to visit or a valid personal reason for being there (such as, "I wanted to"), sanctuary mandates that a cop cannot arrest you until after you’ve finished grieving.
Tag along with a wild bachelor party
How to pull it off: Montreal is famous for being one of the wildest cities on earth, so it’s no surprise that it’s a hotspot for bachelor parties. As you’d expect, there are a bunch of illegal activities that can go down at a wild bachelor party. As the good folks over at Connected Montreal explained, there are many strange laws against everything from eating sushi off of a naked woman, to having topless women in the back seat of a limo, to bringing in a black-market keg. Maybe do them anyway?
Laws you’re breaking: Public intoxication, indecent exposure, seatbelt violations, and a slew of other infractions depending on what sort of debauchery you get yourself involved in.
Bang on some drums at Tam Tams
How to pull it off: Tam Tams is a weekly phenomenon in Montreal during the summer months (or at least when the weather is nice enough). People gather every Sunday at Mount Royal to hang out, play bongos, hacky-sack, or whatever else you can possibly do outdoors. One thing is constant, and makes this date an illegal one: most everyone is either drinking or smoking weed. It's not clear why or how, but cops turn a blind eye to all this activity and allow hundreds of people to get faded in broad daylight.
Laws you’re breaking: Public intoxication, but it’s fine for some reason?
Check out the graffiti at the CN Wellington Control Building
How to pull it off: The tower, which was built in 1930 to control railways, has been all but abandoned and rendered useless since 2000. Since then, it’s become a popular location for graffiti artists to express themselves. It’s a cool spot to bring a date and appreciate the sights together, but it’s also a great abandoned location, perfect for urban exploring.
Laws you’re breaking: Trespassing, and vandalism if you decide to tag the building.
Sneak into Osheaga Music Festival
How to pull it off: One of Montreal’s largest summer attractions is the Osheaga Music Festival, which features some of the largest names in music spread over a three-day span. The event habitually crams herds of people into Montreal’s Parc Jean-Drapeau, and it seems like more and more people show up every single year. This past year, you could hardly even move. It was like 200,000 packed into a sardine can. That’s because a shocking amount of people snuck into the festival, either by hopping a fence without getting caught, or by paying off security to let them in a back entrance. So, go have a great day seeing some of your favorite artists, but don’t pay for the full ticket price like the rest of the population.
Laws you’re breaking: Trespassing, extortion
Go golfing at UFO Golf Laval
How to pull it off: This one is somewhat of a hidden gem. During the summertime, Golf UFO is a course that stays open until 3, sometimes 4am. Also, the prices are more than reasonable. Furthermore, the holes are all par threes, so it’s not the most challenging. It's basically begging you to sneak a couple drinks in your bag and have yourself a tipsy round on the links.
Laws you’re breaking: Public intoxication
Go skinny dipping in Beaver Lake
How to pull it off: Beaver Lake is one of Montreal’s most beautiful attractions. So, what better way to bask in its glory than to take off all your clothes and go for a dip in the likely filthy water? The odds of you getting caught are almost certain, but it's guaranteed to make for a quality story.
Laws you’re breaking: Indecent exposure
Attend a Habs game in Leafs attire
How to pull it off: There’s nothing Montreal takes more seriously than their hockey team, the Habs. While there aren’t technically any laws against wearing Maple Leafs (or any other team’s) attire to the Bell Centre for a game, it may as well be the most illegal act in Montreal. The cops won’t enforce this rule, but the people most certainly will. This is probably the most dangerous thing you can do on this entire list.
Laws you’re breaking: None, but get ready to be punished regardless.
Sign up here for our daily Montreal email and be the first to get all the food/drink/fun in the City of Saints.
Tyler Lemco is a writer from Montreal, Canada. He enjoys burgers, sports, cheeseburgers, music, and bacon cheeseburgers. Follow him on Twitter or all other social medias @tlemco.