on pretty crying
an origin story, a confession, and a new name
Are you of the age where reading teen magazines like YM and Seventeen is a core memory?
I certainly am.
Sprawled out on a blanket on my best friend’s lawn with a slurpee, or curled up on the couch with a cup of tea in front of my favourite soap (All My Children, obvs) I’d head to the embarrassing moments section first and get the schadenfreude out of the way.
While the vicarious trauma of these stories stuck with me (never have and never will be risking a pair of white pants, that’s for sure), the familiar sameness of these anonymized girlhood experiences did too.
How relatable to make a fool out of oneself in front of a crush, to cringe as a staticky pair of undies fall out of a sleeve in the middle of math class, bumble an accidental innuendo in a high-stakes public speaking moment.
These columns have been on my mind lately because in a way, a humility-inspiring (okay, fine, embarrassing 🤣) moment spurred the new name of this publication, and I kind of feel I owe you an explanation.
But first, to understand this story, you need to know two things about me.
One: I’m a teacher.
If you know me know me, you already know this. (A hilarious side note here is that I chose this career under the assumption that as a teacher I would have lots of “free time” to do other things I love, like write. Summers off, workday ending at 3pm, right? Wrong.)
Yet, despite the debunking of that myth, I’ve never once looked back. And for the last almost decade, I have worked in a high school alternate program for academically capable youth who have struggled. I have the privilege of working with my students for two years alongside the best co-workers one could ask for. We compare our program—staff and students alike—to being one big family. The job really takes it out of me sometimes, tbh, but it also never fails to give back.
And, two: I’m a Type A late-diagnosis ADHD anxious Millennial thought daughter…
Which is to say, I feel things deeply. Sometimes painfully so. A single pom-pom once fell off a cheap polyester scarf I was wearing and when I noticed and looked back to see it bereft on the rainy sidewalk, I teared up and trudged back in the rain to “rescue” it. I know.
With those two facts in mind, it hopefully makes sense that the end of a school year inevitably brings for me a tempest of feelings alongside the celebrations. Last year was no different. The pressure of all of The Things culminated in a perfect storm at the end of year staff “festivities” (on a day I skipped lunch, no less).
I’ll spare the microscopic details—though not for a lack of having overthought them far too many times—and just explain that while debriefing the ups and downs of the school year with colleagues late that evening, big feelings spilled out on all sides.
Mine.
Theirs.
More of mine…
It was one of those interactions that feels necessary and cathartic but also maybe a little too raw. (I do ponder as I type this if this feeling is perhaps a Type A late-diagnosis ADHD anxious Millennial thought daughter phenomenon. Please comment below if this is the case.)
The next day, rehashing the tearful discussion with a dear work friend, I expressed how I was happy we had all cleared the air, but wished I hadn’t been quite so… emo.
She considered my point with kindness as I waited for her sage advice.
“But Sarah,” she said, utterly serious. “You’re so PRETTY when you cry!”
As the ridiculousness of her statement registered with me, we dissolved into laughter, the uncontrollable kind that spiralled until we forgot why we were laughing in the first place.
And thus, the notion of the pretty cry was born.
You know, one of those moments packed with both beauty and ugliness—the levity and weight of being human so much to bear—that all you can really do is laugh.
I vowed to reach for this memory of when burnout + breakdown = comedy, to look for the lightness and humour of even the most unexpected moments.
And, when I decided more recently that I needed a refresh to this space, the name pretty cry felt… perfect.
This all came back to me again recently when Catherine O’Hara, a comedic icon, sadly passed away.
Headlines remembered her genius, her charm, her multitude of roles. To me, none of this could be separated from how beautifully she played women who felt things deeply. Women who cried, ranted, loved, spiralled, and were still magnetic.
Pretty, even in the mess of it.
Catherine reminds us that big feelings and sharp humour aren’t opposites so much as they’re sides of the same coin.
Which is what I’m trying to capture here.
I want to squeeze the life out of my “free time” while staying present and grateful for a fulfilling and challenging career.
I want to write and make things. Here and other places too.
I want to keep feeling everything way too deeply while never forgetting to find humour in the depths.
And, I want to make you laugh.
