Funny Date Ideas in Toronto (Laugh at First Laugh)
Have a laugh this Valentine’s Day. Toronto is full of funny date ideas that will make your heart laugh with glee, from comedy shows and arcade games to skating wipeouts and roller rinks that feel like a throwback. If you’re looking for a Valentine’s date that actually breaks the ice, laughter is a pretty great place to start.
Looking to break the ice (pun intended, we've been in a deep snowy freeze... sprinter is bound to come soon!) without awkward small talk? Toronto is packed with quirky, haha date spots that do half the work for you. Here’s a quick, skimmable guide to the funniest date ideas in the city.
🎤 Comedy
The Second City Toronto
An iconic comedy theatre known for improv and sketch shows. ( Legends like, Catherine O’Hara and John Candy began her career at Second City Toronto)
Comedy
Spend a night filled with laughter at Cupid Comedy. Or, you can catch a show ( Sketch, Improv, Alternative, Stand-Up Comedy) seven days a week at the Comedy Bar. Just remember front row seats get a little attention. 😘
Museum of Illusions Toronto
Dating can be a reality, not a virtual illusion.
Snakes & Lattes
With a few locations around Toronto, it’s an easy go-to date. I even know someone who met their match at a game café. Makes you wonder if they were playing ROM COM - A Trivia Game for a Night In... at the game's cafe?
Arcade Bar
I used to hang out at places like this as a teen. All my hard earned job money went straight into those quarters. Check out Tilt (great name! How many times did taht pinball get stuck?) Arcade Bar.
They even have Donkey Kong, Frogger for some retro fun!
Pilates (kitty)
Awww! There is pilates, but how about pilates, and then cuddle with a kitty?
Indoor Playground
Why not check out this place, Pursuitocr... An indoor playground for adults with obstacle courses, tricycle races, and a giant ball pit. Wouldn't falling into a pit of balls be funny? 😂
Ice Skating
Skating at Nathan Phillips Square can be unintentionally hilarious in the best way.
It has all the ingredients:
• Wobbly first laps
• One person pretending they “used to play hockey”
• The other clinging to the boards like it’s a life decision
• That iconic TORONTO sign glowing in the background like a dramatic movie poster
Roller Skating
Last but not least: roller skating
Because nothing breaks the ice faster than watching each other relearn balance in real time. I know there was free roller skating at Union Station, so check it out: https://torontounion.ca/tdunionwinter/roller-express/ and have fun!
Waddup to Roller World in Scarborough!
Happy Valentine’s Day, and whatever you do, don’t eat spaghetti on your first date. Save the pasta for the next one!
