I’ve always collected cities in much the same way I used to collect sex partners. In fact, my relationships with cities parallel stereotypical love affairs in many ways. Some are quick flirtations (Seattle, Atlanta) and some (New York, Los Angeles) are just masturbatory fantasies that I’d probably despise in real life even if they were attainable. But my most serious relationships have been with San Francisco, Pittsburgh, and Toronto.

I’ve told many versions of my San Francisco story. We’ll call this plotline “true love gone wrong.” I loved that place so very much, and for many years I thought we’d spend the rest of my days together. It was a love like I’d felt for no other city and I allowed myself to be blinded to all its many, MANY faults. And that’s why it was not to be. I changed, and San Francisco changed, and I realized that much of what I had loved about it was not real to begin with. It ended badly, and I’ve come to realize that San Francisco and I will probably never really be friends. I get the sense that San Francisco is OK with that; it attracts thousands of new friends every year and will no doubt get along fine without me.

Pittsburgh was very different for me. It was always sort of a side attraction, never my primary love (nor residence), and that may be what has allowed us to stay friendly despite some tense moments. Pittsburgh is the classic “fuck buddy” and the only real problem surfaced when things started to get a little too serious. Fortunately, we got past the awkwardness and I think we’ll be just fine now with our very causal but mutually satisfying arrangement.

And then there’s Toronto. It’s the closest I’ve ever come to what I felt about San Francisco. But I’m not sure I could ever make another commitment like that. Maybe Toronto is the idealized “long distance relationship”; I love it all the more because it’s a convenient escape from my everyday routine–one that I can have in small doses pretty much whenever I want it–and leave the rest to fantasy. Toronto can be my “happy place.” When I feel sad or lonely or just plain overwhelmed by life (which happens a lot lately) I can escape to that little fantasy world–or sometimes even to the actual place. I never have to deal with commuting to work or fighting my way through lines at Loblaws every week, etc. In short, we don’t have to wake up next to each other everyday.

I’m not sure what would happen if Toronto and I ever got serious. I’m a little scared of the idea and am not at all prepared to be hurt by another city. And it’s not terribly realistic anyway. Legally, I could move there tomorrow. I have my Canadian permanent residency. Finding employment and building a life would be another story altogether. But that hint of possibility without the attendant expectations may be be what I find so enticing about Toronto. Plus it’s a pretty sexy place in my view.