Cowboy boots, 21st century love and the road less travelled


I always wear my cowboy boots on my business trips to Toronto.

I don’t know whether your neck of the woods has a city that thinks it’s the centre of the universe and disses everyone who’s not from it—probably, eh? And then, the flipside: a city that knows it’s not the centre of the universe and works harder, parties harder … and has a bit of an inferiority complex in regards to the more sophisticated, snotty older sibling? It doesn’t help that that more sophisticated, snotty older sibling glories in putting down the upstart younger one—nevermind that the younger one, maybe, actually has more talent, a better job, a snazzier car and, damn straight, a better quality of life… but still isn’t the parents’ favourite?

That’s Toronto and pretty much every other city in Canada, especially my hometown of Calgary. As a Calgarian who has lived in Warsaw, Rome, Berlin, Paris, London and Montreal—and spent some time in New York, hush, we don’t need to mention my age at the time—I find Toronto’s attitude… cute.

I love visiting, don’t get me wrong. I’ve got fave clubs, restaurants and galleries—there a lots of benefits to being the biggest and having that population density. But when the city puts on its attitude—which it does as soon as you tell it you’re from Calgary—I like to hitch up my skirt, look at my boots, and pay homage to Nancy Sinatra.


I’m in Toronto for six days, three pleasure, three business, although everything gets all mixed up in the end. I’m in town chiefly to visit my beloved and to try to figure out how, or even if, we’re going to navigate this phase of what has never been a typical relationship.

Love in 2021 looks like this, by the way: you leave your cat in the care of a new love while you go visit the one who left the city but not your heart, and nobody thinks it’s weird. Except possibly your parents, so like, let’s not talk about it.

You: You’re blogging about it.

Jane: Totally different. Hush. You’re breaking my flow.

You drive me to the airport at 4:30 a.m., and that’s also 21st century love, isn’t it, anam cara? Moments like this, I do think that we are changing the world, dismantling some of its most cherished assumptions one act of heartfelt kindness, love, desire at a time.


I don’t know that I get any clarity as such during my visit. But I think a lot of things, all of them true.

First—there is no substitute for face-to-face, flesh-to-flesh contact. Professionally, personally, I don’t care: Teams, Zoom, WhatsApp, Telegram, they’re barely methadone. Sit across from me over a cup of coffee for 15 minutes, and we’ll have moved our relationship forward 75 Teams meetings. Kiss my eyes once and it’s worth a thousand texts.

(To clarify, the kiss my eyes comment is personal, not professional. Just in case any of my new co-workers are reading: I am aware there is an HR manual, and it’s pretty clear: no eye kissing in the workplace.)

(Although I do occasionally send “smooches” to my director via text in response to compliments and forgiveness. Maybe I should stop that.)

(Where was I?)

(Here: There’s no substitute for face-to-face, flesh-to-flesh contact.)

Second—Toronto traffic is unadulterated hell. I don’t remember how Dante splits up the circles of hell exactly, but downtown Toronto, in a car? This is where the counterfeiters, hypocrites, grafters, seducers, sorcerers and simoniacs are punished.

And this is during the pandemic.

Third—the view from my Toronto office is to die for.

Fourth—for me to have the sort of life in Toronto that I have in Calgary, I would have to earn four to ten times as much as I do now.

Also, did I mention the traffic?

Him: Alternative–the flight was super cheap.

Fifth—children. Which is really the first and the final, and while one might be in Kelowna right now, and another planning a move to Vancouver, the little has at least six more years of Calgary growing to do, and, yeah, this is why I’m here to visit, and nothing more.

Him: I did mention the flight was super cheap…

Sixth—We’ve never actually spent six days together, 24/7 or as near as, and, fuck, by day three, I need my space back and so does my love, although when I ask him if it’s been too much, too long, he gets angry.

Seventh—I have a fabulous time (mostly) but I miss my kids, my friends, my life—my new love—with a shocking ferocity.

Eight—I’m in tears and pieces and utterly heartbroken, again, when I have to leave, but also at peace.


A frenemy once told me that whenever I’m faced with a choice between two things, I always choose the harder one. Even back then, I suspected they were right; right now, I choose the harder thing again and again. I know how the easy thing will go. How boring is that? So. Let’s try this. Let’s suffer, in this new way, for a while.

Him: Suffer?

Jane: None of it is easy.


None of it is easy, but, actually, truly, honestly? I’m really happy.

True story: but every time I start to talk about how I’m actually pretty happy, I start crying.

That doesn’t make the statement untrue.

I’m walking a hard path sometimes, but, really… I chose it. And I’m (mostly) happy.

A little heartbroken, but perversely, even that feels good.

Him: Masochist.

Jane: You know it.

The cowboy boots make it all easier.



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