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Plan the Perfect Summer Date in Toronto

In a city filled with seemingly endless things to try, planning a fun date should be simple. When the sun is out and the pavement is hot, try something other than the typical dinner and a movie. See the stars, checkout a comedy show, or even go to the drive-in. Check out our list of the perfect summer date ideas below.

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Stand in Line for Ice cream

Try making the most out of standing in line by using the time to get to know your date. This is a great opportunity for an ice breaker, plus it’s less awkward knowing you have a mutual end-goal (that being ice cream). Bang Bang Ice Cream on Ossington usually has a solid line every weekend.


Go for a Bike Ride Along the Waterfront Trail

Toronto’s Waterfront Trail technically runs from Etobicoke to Scarborough, but you can go east of Scarborough if you’re daring enough. A bike ride is a great idea for a date and Toronto couldn’t make it any easier for you. Pack a picnic lunch, map out some good ice cream stops on the way, and enjoy a scenic ride along the lake.

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Rent a kayak and go for a paddle

There’s only a few weeks of summer left (I’m sorry) so get out there and enjoy Toronto’s most beautiful feature — Lake Ontario. Enjoy the lake as it glitters beneath the August sun (take that, poetry) and easily plan a fun afternoon for your date. Toronto Adventures, Mountain Equipment Co-Op, and Harbourfront Canoe & Kayak Centre all offer Toronto kayak rentals. Toronto Island is also officially open, so pack a lunch and have a picnic on the island to break up the afternoon.


Check Out an Improv Show

They say the key to any good relationship is laughter, and what better way to test the waters on a first date than by seeing if you share a sense of humour? The Second City Theatre in Toronto is an improv and sketch comedy theatre and bar that always has something fun happening on their lineup. Plan a night of beers and an improv show for a guaranteed fun time. You can check out a full schedule of shows here.

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Watch an Outdoor Movie

Grab a blanket, pack a few snacks, and maybe throw in a bottle of a little something to drink, and enjoy an outdoor film under the stars. This is a fool proof date idea. Christie Pits, Regent Park, 99 Sudbury, and Harbourfront Centre all offer movies under the stars.


Hang out at Buskerfest

For four days, Woodbine Park is transformed into a land of games, entertainers, great food, and otherworldly installations. Toronto’s BuskerFest is a solid way to spend Labour Day Weekend with a date. Plus, it’s free to attend!


Pedestrian Sundays at Kensington Market

On certain Sundays throughout the summer until October, the roads running through Kensington Market are shut down to allow pedestrians to walk freely. This is a great idea for a chill afternoon date. Stroll around and browse everything Kensington has to offer while getting to know each other through casual conversation. Plus, it’s free to attend. There are only three more Sundays to enjoy this event: August 27, September 24 and October 29.


Look at the Stars at the Dunlap Conservatory

In 1935, The Dunlap Observatory was home to the second largest telescope in the world. Now, it still boasts the largest optical telescope in Canada and provides a unique opportunity for Torontonians to explore the night sky without majoring in astronomy. Dunlap’s drop-in nights (whether permitting) are a really unique way to spend a date. What better way to get to know someone than by trying something new together?

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Share an App on a Cozy Patio

Plan a night of beers and apps on one of Toronto’s many patios. This is an easy thing to do on any night of the week while also fostering good conversations and relaxed vibes. Checkout our list of Toronto’s best patios for inspiration.


Go to a Drive-In

We’re lucky to have historical things called drive-ins around the GTA. Visit The Docks, Toronto’s only remaining drive-in, or take a drive out to Oakville’s 5 Drive-In or Newmarket’s The Stardust. Grab some popcorn and tune your radio while feeling like you’re in Grease (or Riverdale for you youngins).

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