I grew up in big cities too, but my liking is actually quite contrary to that. For a good time, I love to head out to the country/more natural areas. Unfortunately Ontario isn't that great of a place for natural attractions. I might head out to Berty's town with a job sometime if possible. Alberta/BC is the kind of place I'd love to be in.
In Toronto, my favorite thing to do is to hit the beaches (Brimley/Woodbine) and just chill there during the summer. The full walk on the Woodbine beach boardwalk is pretty awesome.
The theaters there are a different experience as well. Small places, with almost no people most of the time. Great place to chill with friends, as you guys will probably be the only ones in the theater
For winter, my favorite thing to do is to head to small towns like Stratford, Fergus, and such. These places look absolutely stunning during snow season. Best place to chill out in a cafe.
I also love taking random late night drives through the country, like those one lane roads. It's pretty creepy, but that adds to the fun. Went out last night actually around 1230 to Stratford through local roads via about 5 smaller towns. There was literally no one except for us on the roads.