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Originally Posted by hipster duck
The "great years" were 2005-2008
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That was a pretty special time for me too. I was in high school then, so too young & poor to get to do
everything I wanted, but that's when I at least got to start exploring the city and experiencing it in a meaningful way - when it was all still fresh and full of unknowns & surprises (also when I joined SSC & SSP!). When you could first discover some lovely little street that you
hadn't already walked down a hundred times before.
I had another round of "great years" from like 2014-2016, when I was finishing up school and was newly independent with a bit of cash, though that was a much different feel and not quite as directly predicated on the excitement of the city itself (it certainly made a good backdrop for a cliched sex-and-drugs 20-something experience).
Still, I feel like the "objectively best" years in Toronto was the late 00s-early 10s. It was dirtier & less polished then, and there were still the vestiges of the quirky city of old; but with enough growth & development to start filling in the gaps and giving it a sense of true metropolitan bustle. That was that moment where cost of living and population growth and quality of life and creativity all existed in near-perfect equilibrium.
Of course, I could also be totally biased and clouded by those being the years of my teens & early 20s...
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I mentioned this in a post a few years ago, but Toronto is not a city that rewards long term relationships. You have your carefree time, and then you promptly get out, almost like you're in a line for some popular attraction. This is mostly a function of the exorbitant costs of living here, but I also get an unscientific feeling that Toronto is a place that doesn't want hangers-on; it welcomes the new and throws out the old, no matter what contribution you made to the city in the past.
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There is a certain transient nature to Toronto, but what you're describing is also more typical of the transplant experience. That is - come when you're young & newly independent; get out once the responsibilities start piling up. Or, you get the types that just seem to perpetually drift from place to place (with who's path you just happened to cross when you were both young in this place).
Having grown up here though, most of my extended social circle is also comprised of locals - and most of them that grew up here are still in the city. With one or two exceptions, those that I've known who left the city were the ones who were never really had any attachment to it in the first place. People for whom Toronto was like your version of Vancouver.
If it's your home though, I think there's just less of even so much as a consideration that it's
possible to live somewhere else.