Last week, I posted a recap of all my favorite Halloween costumes from the first 30+ years of my life. After my ode to The Bride from Kill Bill in 2005, I took a bit of a break from celebrating Halloween, and going out dancing, and getting out much at all, to be honest… It was a weird time!
From 2010 until 2018, I worked two jobs, mostly from home, played a lot video games, and did a lot of writing. So it wasn’t a totally lost decade, but then 2018 hit, I started roller skating and giving a shit about fitness for the first time in a while, and entered a whole new era of extroversion.
To be fair, I did attend a few office Halloween parties in those in-between years, but they were pretty low effort. One year, I pulled my old art school leather jacket out of storage and dressed as Sandra Dee from Grease.
But, like I said, everything changed in 2018. Rodger started playing hockey again, and we met a solid handful of new friends who still make up the core of our social group today. I started skating, and eventually met my best friend, Helen, and a group of burlesque dancers who are a huge part of my life today.
Back in fall of 2018, just a few days before Halloween, we met a couple who reignited our spirit of excess, especially dressing up in ridiculous outfits, and it all started with a challenge: Meet us for drinks dressed as your favorite member of KISS.
For both of us, that was an obvious choice. We had actually done this once before, back in 1999 when KISS came to Roger’s Arena in Vancouver on New Year’s Eve. We decided that was the best way to ring in the new millennium, and ride out any potential fallout from the much hyped “Y2K bug.” (If you’re too young to remember that, google it sometime… It was a fun, harmless scare to kick off a much scarier decade to come!)
Anyway, back to 2018, the four of us decided that, given the late October weather and the fact that we had just a couple of days to prepare, the best way to approach the costumes would be to focus on the makeup and keep the costumes low-key. The album “Dressed to Kill” became our inspiration.
2018: KISS: Dressed to Kill
We arrived and the bartender immediately broke into a smile and pointed us to a back table. “The rest of the band has already arrived.”
We proceeded to get very drunk with our new friends, took tons of pictures, bonded over shared histories, and quickly became a quartet that lasted almost three years. We took trips together, went to punk shows, organized elaborate dressed up dinners at each other homes, went dancing, went skating, played games, and ironically referred to ourselves a “fourple,” which confused the hell out of people who thought we must all be sleeping together…
Which we were not!
But in all other ways, we were as close as four people could be—two couples in our 40s with no kids and one cat each, who loved good food, music, road trips, and each other… until Covid ruined everything.
I’m not going to get into that history, but it’s why I don’t have any pictures of the four of us together. By the time the fourple broke up in 2021, we all blocked each other and deleted every shared experience from our collective devices and online services. Such drama!
But I think sometimes, even when you’re old enough to know better, you experience that heady adolescent kind of relationship that burns so brightly and takes over everything, that when something changes in the rarefied environment that made it possible, it can’t sustain itself. At least, that’s the sanitized, shade-free version I’ve settle on all these year later.
2019: Overlook Hotel Twins
And but so anyway, those years produced some great Halloween costumes! In 2019 we decided to dress as the scary twins from The Shining. The other day, I spent about an hour trying to find some actual photos from that night, but they’ve all been purged from the internet, and my old laptop is basically a brick that refuses to communicate with modern devices.
Just as well! I asked Chat GPT to recreate the moment, and recast my former friend as the preternaturally likeable Zooey Deschanel.
This is a great use case for AI, in my opinion. Here’s what Chat GPT had to say about rewriting history:
“You have officially reclaimed the creepy twins.
The original memory can stay in the archives of Things We No Longer Need to Give a Fuck About. The new canon is that you and your imaginary Zooey Deschanel doppelgänger are two fabulous, slightly unhinged women who have materialized in the Overlook Hotel to judge everyone’s life choices.
And honestly? There’s something genuinely satisfying about taking an experience that has become tainted and making something new out of it. You don’t have to pretend the friendship was fine, recover the old photos, or preserve a single pixel of that era. You get to keep the ridiculous costume idea, the Halloween fun, and the creepy-twin aesthetic without keeping the person attached to it.
The dresses survive. The friend has been written out of the movie.”
2020: Harley Quinn
This is more or less self-explanatory… “Birds of Prey” had just come out and Margot Robbie rocked the house as the crazy-sexy-coolest heroine in the DC universe, Harley Quinn. We partied at home because Covid, and for the first time since my 20s, I actually had the abs to pull off a costume like this… win win!
2021: Sexy Pirate
Around the same time as all the “fourple” drama was happening, we were becoming great friends with our upstairs neighbors, a very cool couple with a huge and diverse friend group, who loved organizing pot luck dinners, game nights and especially, murder mystery parties!
The next few years, all our Halloweens revolved around studying PDFs of our characters and putting together costumes to play our parts at these epic parties.
The first year was 2021, and the theme was witches vs vampires at a Halloween gala, so we all got assigned a “clan” and then just dressed up in costume. Rodger was the head of the vampire clan, but dressed as the grim reaper, and I was a witch who fell in love with the vampire and defected to their clan, but dressed as a sexy pirate. Fun!
2022: Sorcerer’s School Murder Mystery
The next Halloween was another murder mystery and our characters were students at a Hogwarts-style school for magicians. I was the smartest girl in school and Rodger was the most popular boy in class… Talk about type casting!
2023: Secret Service Agents
This year’s murder mystery was a political thriller, and Rodger and I were both cast as secret service agents protecting the President. In the first act of the game, I got shot in the line of duty while the President was giving a speech.
My dramatic death scene was made all the more poignant by Rodger’s swift improvisation skills (because of course, I had to keep my imminent “death” a secret from him per the rules of the murder mystery game).
He rolled with it brilliantly, kneeling to feel my pulse and shouting at the crowd to clear a path, while he swept me up in his arms and carried me from the room. Some of our fellow party-goers couldn’t help breaking character, filming the dramatic death scene and even cheering a little as Rodger reenacted “The Bodyguard” with my lifeless body draped over his arms.
After my death in the first act, I did get to keep playing as a second character, but I don’t have any pictures of that. It was basically the same costume, sans jacket and tie, with my hair down and messy. It turned out, I was murdered by our fellow secret service agent, who was actually a spy working for the opposition.
2024: Flapper Tennis Star in the Jazz Age
The following year’s murder mystery was held at a local distillery on Granville Island, the perfect setting for a night of intrigue and treachery set in the roaring 20s. I was a Jazz Age flapper tennis star, and the night was star studded with fantastic fringed skirts, beaded accessories, feathered headdresses, and cigarette holders.
2025: K-Pop Demon Hunters
Last year, my bestie Helen decided we were going to dress as the very timely “K-Pop Demon Hunters” for Halloween, and she ordered an elaborate (and it turns out, very heavy) lavender Rumi wig from Temu to make the costume complete. (We did have a third member, but she unfortunately caught the flu right before Halloween.)
Helen is a kindergarten teacher, so she wore the wig to school, much to the delight of all her students, who were universally obsessed with the movie. In fact, she told me in the month leading up to Halloween, sometimes the only way to get the class to calm down after their lunchtime blood-sugar energy spike was to put on the song from the movie and let them all zone out.
I was only too happy to take on the role of Mira, the smart ass member of the trio with the long hot pink hair. No wig needed… I only needed the flimsiest of excuses to go full-on magenta for the full season. My wild hair color lasted from Halloween to New Years without substantial fading.
And that brings us up to the the present day! The last decade of Halloween costumes has been awesome. This year, my bestie and I are going to Dooms Night, a huge costume party at the PNE. We’re going as sexy angels lol.
With one week left before Halloween 2026, what are your plans? Tell me in the comments!