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Roommate Roulette

  • Writer: Shannon
    Shannon
  • Sep 2
  • 5 min read

Roommates: the Russian roulette of your twenties. Sometimes you spin the wheel and land a gem. Other times, you land a human cautionary tale who thinks “doing the dishes” means hiding them under their bed.

While my friends were debating pram colours and wallpaper samples, I was spinning the roommate wheel every six to twelve months. Here’s what I got.


🎲 The Good: Wine Nights & Wingwomen


Scene: Thursday evening, post-breakup meltdown.

I’m in my pajamas, mascara smudged, clutching a block of chocolate like it’s a life raft. My roommate, Jess, appears at the door holding two glasses of wine.

Jess: “Okay, tell me everything. Start with how much of a trash bag he is.”Me: “He ghosted me after three months… and I wasn’t even attracted to him.”Jess: [pouring the wine to the brim] “Men are weak. Cheers to us.”


Jess wasn’t just a roommate. She was my built-in wingwoman, hype-girl, and crisis counselor. Together we turned lonely nights into movie marathons, grocery store runs into dance parties, and bad Tinder dates into comedy routines.

She also played guitar. Which meant our wine nights often spiraled into accidental concerts — hours of us making up songs about boyfriends who ghosted, nightmare bosses, or people we didn’t like. We’d belt them out like our lounge room was Madison Square Garden, laughing until the neighbors probably considered calling Noise Control.

When invitations said “plus one,” she was mine. And when life felt heavy, she filled the house with laughter, snacks, and just enough sass to keep me moving.

Lesson: sometimes, a good roommate fills the space of a partner — without the drama, the ghosting, or the bedframe symphonies.


🎲 The Judgy Fridge Note


Scene: Tuesday morning. I open the fridge, eyes locked on the carton of eggs I’d bought with the last $4 in my account.

Except there’s a Post-It stuck to it. Written in aggressive bubble letters:

“Do you know the suffering you’re funding by buying caged eggs?”

The kicker? It wasn’t even from my roommate. It was from her friend who had stayed over one night.

Me (to the Post-It): “Do you know the suffering I’m funding just trying to pay rent?”

At the time, I was broke-broke. We’re talking ramen noodles and bulk pasta broke. Free-range eggs were a luxury. Meanwhile, I was being morally shamed inside my own fridge by someone who didn’t even live there.

Lesson learned: sometimes the only thing worse than a roommate is their self-righteous guest.


🎲 The Bedframe Symphony


Scene: 11:30 p.m. sharp. Every. Night.

I’m tucked in, scrolling Facebook (because this was pre-Instagram doomscrolling). Suddenly, the ceiling starts squeaking. Loudly.

Me (to myself): “Oh great, they’ve started Act One.”

The rhythm built like an orchestra. Crescendo. Crescendo. Then silence.By week two, I was humming along like it was the soundtrack to my insomnia.

If Spotify had playlists titled “Thin Walls Vol. 3,” this would’ve been track one.


🎲 The Over-Sharer


Scene: Monday morning, before work. I’m in the kitchen, half-asleep, clutching coffee.

My roommate waltzes in wearing nothing but a towel and immediately launches into her weekend recap:

Her: “So, I went on a date with this guy from the gym. We ended up at his place… and let’s just say I learned new uses for coconut oil.”

Me (still stirring sugar into my mug): “It’s 7:15 a.m. I haven’t even processed toast yet.”

She had zero filter. Every minor detail of her life — dates, bodily functions, family drama — became breakfast table entertainment.

By month three, I knew more about her digestive system than my own.


🎲 The Wannabe Worker


Scene: Monday morning.

At 8:30 a.m. sharp, my roommate would march out the front door in a button-up shirt, holding a laptop bag. He’d wave goodbye like he was heading off to conquer corporate life.

By 9:05, he’d slink back in, kick off his shoes, and spend the day in pajamas on the couch watching Judge Judy.

Apparently, he “worked in finance,” but in reality, he couldn’t hold down a job longer than two weeks. When his parents called, he’d lower his voice and pretend he was “at the office.”

Meanwhile, I was hustling nonstop — full-time work in childcare by day, nannying on the side by night — just to scrape together enough for rent and groceries. He was living his best fake-CEO life, eating my pasta and leaving “meeting notes” (aka doodles) on the kitchen table.

Lesson: there’s nothing worse than splitting bills with someone who’s cosplaying employment.


🎲 The Health Guru Gone Wrong


Scene: Sunday brunch at home.

My roommate is blending spinach, almond butter, and… was that beetroot?

Me: “Is that… edible?”Her: “It’s healing. It aligns my chakras.”

She was dating a Buddhist monk-in-training, so naturally, our apartment became a temple of incense, mantras, and long lectures about how “meat is trauma energy.”

The problem? Her devotion to health and serenity was rivaled only by her devotion to candles.

One night, she left one burning. I woke up to the fire alarm, the scent of scorched kale chips in the air, and her calmly chanting in the lounge.

Her: “It’s fine, flames are cleansing.”Me (sprinting with a wet towel): “CLEANSING? The curtains are on fire!”

Lesson: health is great, but fire extinguishers are greater.


🎲 The Best of the Best


Not all roommates were cautionary tales. Some of them became family.

They were the forever friends who turned late-night wine into therapy sessions. The ones who stayed up watching trashy rom-coms with me after a breakup. The ones who cheered on my dating disasters like they were front-row at a sporting event.

They were my automatic plus-ones to parties, my partners-in-pizza-orders, my co-conspirators in binge-watching reality TV.

And on the loneliest days, when I ached for a relationship or just someone to come home to, having a roommate filled that gap in the cutest, funniest way. Sure, they didn’t bring flowers or remember anniversaries — but they remembered to buy chocolate on bad days, and sometimes, that’s even better.


The Lessons


Roommate roulette wasn’t just a lifestyle. It was an education:

  • Always guard your leftovers.

  • Earplugs are essential survival gear.

  • Passive-aggressive fridge notes are an art form.

  • There is such a thing as oversharing.

  • Health is important — but so are fire alarms.

  • Never trust someone who “goes to work” but comes back five minutes later.

  • And the good ones? They’re worth keeping for life.


Why It Matters

Those years were messy. Lonely. Loud. And yes — ridiculous. But they were mine.

While my friends were posting their nursery setups, I was posting memes about shared houses. While they had stability, I had stories. And honestly? Those stories built me into someone who can laugh, survive, and keep spinning the wheel — no matter how chaotic it gets.

And sometimes, the wheel lands on a jackpot — a roommate who becomes family.



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1 Comment


Jessy Woolston
Jessy Woolston
Sep 02

I fucking loved reading this!! Poetic and symbiotic with the early millinum experiences shared by many young budding women of the time!


You're an absolute icon Shan!!! My love!

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