By your criteria, I think you'll find a fine time in Toronto, Montreal, Ottawa, or Vancouver. There's no reason you couldn't find the time you're looking for in either city.
I'll still put my vote in for Montreal though. I was born and raised in T.O., and have lived in Ottawa for years (I've only visited Vancouver, but had a really good time there as well). But while there's nothing wrong with any of those cities there's still nothing quite like Montreal.
Go there. There's old. There's new. There's nightlife. There's debauchery. And the most naturally beautiful people in the world (IMHO).
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