You don’t need to be in love to enjoy the cheery deliciousness of a day with a dark history that’s all about romantic love. It’s probably better if you’re not — after all, aren’t the best songs about love the ones about its lack or loss? And aren’t the most memorable romances also comedies in the truest sense?
Regardless of whether you’re spending this weekend in the company of a special someone or stoically barrelling forth like it’s any other day, we’ve got you covered.
From tales of a Timothée Chalamet haircut gone wrong to a Valentine’s Day landlord intrusion, Tyee staff are here with their real-life stories of flower deliveries in the poufy-haired financial district of 1992, high school matchmaking machines and a Polaroid that said a thousand words.
Enjoy! Share your funny Valentine memories in the comments.
Dump the chocolates and run
When I was a teenager, I worked evenings and weekends in a White Spot kitchen, scooping ice cream for milkshakes and slowly honing my hatred of all things dairy.
The kitchen was mostly staffed by rowdy, foul-mouthed men who liked to whip sizzling-hot french fries at one another and break into loud song while flipping burgers.
Mostly they left me alone.
But one memorable Valentine’s Day I was approached by a suddenly bashful co-worker, who wiped his hands on his greasy apron before handing me a box of brightly wrapped pink and red chocolates in a heart-shaped box.
“Would you, uh, like to be my valentine?” he asked, smiling at me shyly.
I stared at the box for a long moment.
Finally I made eye contact.
“Uh... I’m 15,” I said, not sure how else to break it to the man that there was more than a decade between us.
I remember the colour draining from his face.
“I DID NOT KNOW THAT,” he said, taking a big step back, holding his hands out as if to stop something.
He threw a horrified look at the chocolates I was still holding.
“You can just have those,” he said, already fleeing.
— Michelle Gamage

A little light Chalamet
A few years ago, I went out to get my hair cut. My hairdresser is wonderful, and the salon is a hip spot in Chinatown. But that day I made what turned out to be a highly questionable request: a cut inspired by the celebrated actor and universal heartthrob Timothée Chalamet. You might have thought I did this on a whim, but I showed up with a mood board and everything, with several photos of the guy for inspiration.
The salon was bustling that day. It turns out it was Feb. 14 — I hadn't been paying attention. Everyone was chatting about their romantic plans while getting sleek new hairdos or voluminous bouncy blowouts.
Multiple people thought I was going through some kind of heartbreak that day. Why else would someone make such a bold choice for their hair, on today of all days? I don’t blame them.
I fully had a Fleabag moment in the salon. You know, the one where her sister Claire gets a ridiculous haircut and wants a refund but then it is revealed that the cut was exactly like the photo that inspired it.
I don’t know if I “looked like a pencil” (as Claire immaculately describes her new look in the show) — more like a Walmart Salman Khan.
The lesson of the day: just because a cool non-binary influencer is saying you can rock a Timmy cut doesn’t mean you should go for it. And celebrity hair is heavily stylized. If you forget that like I did, you might be wearing a toque all month.
I also learned that, while hair is everything, haircuts aren’t forever (thank God).
— Hina Imam
Say it with flowers?
When asked about my worst-ever Valentine’s Day I can think of a bevy of choices, but one V-Day massacre reigned supreme.
Let me set the stage for you. It’s 1992. My twin sister and I are living in a co-op in Gastown and trying to finish our undergrad degrees at Simon Fraser University.
We took as many courses as we could at the new downtown Harbour Centre campus because it was a 10-minute walk from home, as opposed to an hour on the bus to SFU Burnaby. Also, the downtown campus was a brand new facility, and things were still being worked out. That meant that if we got to the computer centre early, we could each claim a station from when the place opened until its closing hour.
At the time, personal computers for students were a way off both in price and accessibility, so securing a spot in front of an SFU machine was a dire necessity.
I’d arrive at the computer station bright and early every morning. So early, in fact, that the security guard eventually asked if I just wanted a key to let myself in.
My sister took this dedication to the facility one step further and got a part-time job in the Harbour Centre basement at a flower shop. Tucked underneath the escalator, directly across from the liquor store, the place was run by a very sweet woman named Sally. The experience sparked what would become my sister’s lifelong interest in plants, flowers and design. Which endures to this day.
We were both in our early 20s at the time and obsessed with relationships, as one tends to be at that age. At the time, I was between boyfriends and writing mournful journal entries about being alone forever, accompanied by sad drawings.
When my sister asked if I could help out at the flower shop with the Valentine’s Day rush, I didn’t hesitate. I needed the money.
So, on the most romantic day of the year, I got there early, as I always do. It was a bit of a madhouse: flowers, cellophane and stuffed teddy bears were everywhere. The shop owner gave me a list of delivery addresses and a heap of bouquets, and off I went.
The first few drop-offs were OK. Lots of squealing women, mostly working in reception in the office towers downtown. After finishing my first rounds of deliveries, I headed back to the flower shop for another load.
Somewhere in this process, the delirious squeaks of joy and mushy sentiment began to pall. Things went precipitously downhill from there.
Soon enough, the deliveries descended into me stomping into offices and yelling, “Here’s your fricking flowers, lady.”
I stopped short of beaning poufy-haired secretaries over the head with a dozen roses. But just short.
By the end of the day, after witnessing so many people getting big flowery protestations of love and eternal devotion, my self-pity had curdled into white-hot rage.
My journal entry that evening reads, “Worst Valentine’s Day, EVER!!!!!!”
It’s a sentiment I still stand by today.
— Dorothy Woodend

Amour ex machina
I was sitting in the middle of Grade 8 French when the teacher started handing out what looked like a pop quiz. They were the usual sheets of machine-readable paper, with bubbles to fill in with pencil to mark our responses to multiple-choice questions.
But when I received mine, I saw it had nothing to do with school: it was a personality quiz for a matchmaking program. Valentine’s Day was near.
Students could fill it out if they wanted to, hand it back to their teacher and, for the price of two dollars, receive a ranked list of potential soulmates among the student population.
It was such a strange thing to receive at school. Why did the school want to be involved in our romantic lives? Why were they welcoming a third party to come in and do business at our place of learning, and for something as frivolous as this?
The school was very strict about anything to do with money, even giving clubs a hard time for selling food for fundraisers. Yet here they were, promoting what was essentially a very primitive dating app.
Of course, I filled it out. There were questions about your studying habits, your hobbies, your ideal boyfriend or girlfriend (tee-hee!) and your physical attributes and star qualities. It was all very heteronormative.
I had forgotten all about this experience. When it popped into my head again recently, it seemed so unreal.
But upon Googling around, I found others who drew the details out from the depths of their subconscious.
Mel Magazine found someone who took the quiz in 1991, who remembered that it printed questions like “DO YOU BELIEVE THAT WOMEN SHOULD WORK (OUTSIDE THE HOME) AFTER THEY ARE MARRIED?” and “IF THIS COUNTRY WERE TO SUFFER AN UNPROVOKED NUCLEAR ATTACK AND WOULD BE TOTALLY OBLITERATED IN A MATTER OF MINUTES, WOULD YOU FAVOR UNLEASHING THE U.S. NUCLEAR ARSENAL UPON THE ATTACKERS?”
Mel also found service providers that offered teachers the option to take part in the school-wide quiz themselves.
Over the years, the results looked a bit better, evolving from something resembling what code breakers used in the Second World War to pink sheets printed in Comic Sans.
We received a list of potential soulmates in our grade and others, as well as absolute opposites.
I didn’t know of anyone actually getting together thanks to the matchmaker quiz, but there was a lot of giggling over each other’s results.
I suppose there’s always some excitement handing our love lives over to machines to moderate our romances.
Who could’ve guessed that one day, everyone would be doing it on the regular.
— Christopher Cheung
A romantic night in renter’s rights
It was Valentine’s Day in Montreal, and my long-distance partner had flown in from Vancouver so we could spend the week together.
I was a student, so finances were tight. We decided to celebrate by cooking a feast for two featuring roast salmon, a cheese board, strawberries in a salad, a baguette and wine.
But the wine and bread were somehow already gone when we were still prepping dinner. So we threw on our boots and headed to a nearby dépanneur to restock.
Fifteen minutes later, we came home to a peculiar scene.
All of the apartment lights were on. All the bedroom doors were wide open. I didn’t have any roommates. This was not how I left the house.
We were creeped out, but the front door was locked. It took less than a minute to confirm there was no one else in the sparsely furnished apartment.
Ghosts?
I learned later it was my scummy landlord. He decided Valentine’s Day was a perfect time to show my apartment that I’d be moving out of once school wrapped up in June.
Apparently he’d knocked before entering, so “it was fine.”
My Valentine’s Day advice is to learn your tenant rights.
— Michelle Gamage
Thanks, Grandma
It was “reading week,” which meant we had a week off from classes and could do what we liked. The time is formally intended for university students to catch up on their studies, but many of us had other priorities. I hopped into the passenger seat of my then-boyfriend’s dusty, disintegrating Plymouth Laser and we left the city for Quadra Island, stopping in Victoria to visit his grandparents on the way up.
I don’t think we remembered it was Valentine’s Day, but his grandmother didn’t forget. She placed a little red foil-wrapped chocolate heart at each of our places at the table. We talked about Nelly Furtado, who had a breakout single on top-40 radio at the time and whose parents lived down the way. They were proud of her.
To mark the bright, beautiful morning before we left, we set a camera on a timer to take photos together on the front lawn. We broke up in a dramatic hail of long-distance phone calls that summer.
A decade later we met for dinner in Gastown, when he was back in B.C. because his grandma had died.
“Remember that morning in Victoria?” he asked. “The photo of the four of us hung framed in their house to the end.”
— Jackie Wong

From a goth in training, ‘Decapitation Day’
My best Valentine’s were the years I vehemently rejected the celebration. Of course, I’m talking about high school.
Valentine’s Day was great from kindergarten to Grade 6; every kid got a valentine and gave one in return, even to the classmates they didn’t like.
But by Grade 7, now in junior high — and in the throes of awkward puberty and related self-loathing — Valentine’s was strictly for couples. Perpetually single until adulthood, I felt excluded.
At first, I was sad and jealous every Feb. 14. But the envy and resentment of being forced to contend with my loneliness took over, and like the Grinch hated Christmas, I grew to loathe Valentine’s Day.
Around Grade 9, I learned that Saint Valentine had been beheaded on Feb. 14. I’d long had a penchant for celebrating the morbid, so I declared to friends and family that I would be celebrating Feb. 14, after all, as Decapitation Day.
Friends got scratched-out store-bought valentines or homemade ones from me, wishing them a happy Decapitation Day.
One year my sister’s Decapitation Day card came with a decapitated doll’s head; I had painted its skin with Wite-Out to look like a corpse. She hung it from her bedroom door frame.
My dad and stepmom thought my renaming of Valentine’s Day was funny, and after years of my gleeful declarations every Feb. 14, even my mother — who hated the doll’s head hanging over my sister’s door — started saying “Happy Decapitation Day!” back.
While I am still not a fan of the forced romance of the day, I’ve backed off trying to change the name or rain on others’ romantic parades.
But that hasn’t stopped old friends from sending me this meme every few years.
— Katie Hyslop
The first Valentine’s dinner of a lifetime
I started dating my now-husband Andrew in the summer of 2001, when I was 23 and he was 25. In the fall, I flew to Prague on my first travel adventure. He joined me a few months later, and in February 2002 we celebrated our first Valentine’s Day together. Andrew had pulled out all the stops, getting us a reservation at a fancy-ish restaurant that was filled with other couples who all seemed so much older and experienced at being a couple.
We felt incredibly awkward as a waiter approached us to take a Polaroid photo (yes, that’s how long ago it was) and we watched as a middle-aged husband and wife posed much more naturally, twining their arms around each other while holding wineglasses, as if they’d posed for many such photos.
“They’re the couple whose children have children,” Andrew quipped later as we talked about how uncomfortable we’d felt being seen and treated as “a couple” and our strange jealousy of the older couple who seemed so much more at ease in the world.
Since then, we’ve celebrated Valentine’s Day on our own terms — going out for dinner not on the 14th itself, but on a date close by that’s more relaxed. One year we ordered in pizza and watched The Princess Bride with our kids.
But now that we’re the couple who have children, we’ve finally learned how to pose for a photo.
— Jen St. Denis
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