I almost didn't recognize my own friend.
I was doing that half-asleep scroll through Instagram Stories — the one where you're not really looking at anything, just watching faces blur past your thumb — when I stopped cold on a photo of someone I've known for six years. Big permed hair. A denim jacket with shoulder pads I'm pretty sure haven't existed in a Montreal store since the Expos still played here. Lighting like a mall photo booth from before I was even born.
For a second I genuinely thought she'd dug up an old family photo. She hadn't. She'd typed a sentence into ChatGPT.
That's the moment this went from background noise to something I needed to understand. My first instinct wasn't "let me write about this," it was "wait, what would I look like" — which is exactly the point. So instead of running the same trend explainer everyone else already has, I tried it myself and asked the one question nobody outside this city is going to ask for you: what does this look like when it's pointed at Montreal?
Strip away the hype and it's genuinely simple: you give ChatGPT a current photo of yourself and ask it to reimagine that photo as though it had been shot in the 1980s. It's not a filter thrown over your selfie — the AI rebuilds the whole picture, new hair, new clothes, a new street around you, different light, different grain. The one thing it's told not to touch is you.
Depending on the prompt, the same photo can come back as a mall-studio portrait, an overexposed family snapshot, or something closer to a magazine shoot — a full AI-generated image mimicking real analog photography, film grain and all. Not a vintage filter. A completely rebuilt frame.
What shoved it into every feed at once is Instagram itself. People post their result to Stories with the "Add Yours" sticker on top, turning one person's experiment into a chain reaction — I watched it happen in my own feed over three days, one post, then four, then everywhere.
It's got the same DNA as the Ghibli-style AI portraits and the AI action-figure craze before it — dead simple, thirty seconds, strangely photogenic. What's different is how personal it feels. A cartoon of you is cute. A version of you that looks unsettlingly like something your mom might've actually kept in a drawer is another feeling entirely.
I think it's one question none of us can actually answer for ourselves: what did I look like before I existed?
Most people posting these weren't alive in 1985. I wasn't. That's the whole engine of the trend, not a gap in it — nostalgia you didn't earn, borrowed from a parent's wedding photo or your dad's stories at Christmas. It hands you a way to actually step into that feeling instead of admiring someone else's version of it.
There's also a real curiosity gap at work — you already know what you look like today, the least interesting photo you could post. A version of you from a decade you never lived through is unknown territory. And Instagram's design does the rest: the "Add Yours" sticker dares whoever's watching to try it themselves, which is how one weird experiment turns into something your barista, your cousin, and half your group chats have all done in a week.
A handful of Montrealers have started posting their own versions, and the local touches are what make them worth featuring — a staircase in the Plateau standing in for a backdrop, a Habs jersey doing more work than any prop could, a snowbank that looks almost too on-the-nose. Here are a few worth a closer look.
This is where most versions of this trend fall apart everywhere else — "the 80s" as a costume with no place attached. A Montreal version needs to feel like a specific neighbourhood on a specific kind of day, not a decade floating in the abstract.
Downtown, Saint-Catherine Street in the mid-80s meant heavier department-store signage and a skyline the condo boom hadn't reshaped yet. The Plateau and Mile End looked nothing like the boutique-and-brunch version of themselves now — working-class, largely francophone, though the exterior spiral staircases on every triplex look exactly the same today. The Metro was already part of daily life, having opened in 1966, but its signage and train cars were unmistakably that era. Winter meant boxier cars half-buried in snowbanks on streets without today's condo towers. And if you want real cultural weight, the Canadiens were in a genuinely stacked era through the mid-80s — which gives a hockey-themed prompt actual texture instead of just a jersey.
None of this needs museum-grade accuracy. But naming an actual street, a real kind of building, a specific season — that's the difference between a photo that could be from anywhere and one that reads, unmistakably, as this city.
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I did this myself before writing any of the above.
Written from scratch for this piece — take them, mess with them, make them yours.
1. 1985 Montreal Street Portrait "Reimagine this photo as a candid street portrait taken in downtown Montreal in 1985. Preserve my exact facial features, skin tone, and expression. Style my hair and clothing in authentic mid-80s fashion with no modern branding. Set the scene against period-accurate storefronts and pedestrians dressed for the era, shot on grainy 35mm film with slightly faded colour and natural daylight. No modern vehicles, phones, or signage anywhere in frame."
2. 1980s Plateau / Mile End "Recreate this as a portrait taken on a Plateau or Mile End street in 1985, standing in front of a classic Montreal triplex with an exterior spiral staircase. Preserve my face and expression precisely. Give me era-appropriate casual clothing and hairstyle, soft afternoon light, and slightly faded film colour. No renovated storefronts, modern cars, or contemporary signage."
3. Montreal Sports Fan, 1985 "Recreate this photo as though taken at a Montreal Canadiens game in the mid-1980s — a vintage-style jersey, period-accurate arena seating and signage in the background, warm arena lighting with visible film grain. Preserve my facial features and expression precisely. No modern jerseys, screens, or contemporary arena branding."
Look twice before you post, and let a great AI photo be exactly that — not proof of anything historical.
An AI recreation isn't a historical photograph and shouldn't get captioned like one. A real archival photo documents something that actually happened; a genuine Instagram post and an AI recreation are both creative work. It costs nothing to add "AI-generated" to a caption — the difference between a fun experiment and something that ages badly.
Tag @MontrealDiaries on Instagram. I'm looking for real Montrealers to feature as this trend keeps going viral — with actual credit, not a repost and a shrug. Standing on the Main, waiting for the 55, leaning on a dep counter in some imagined 1985 — send it over. I'd rather build the next version of this story around real local photos than hypothetical ones.
Je suis Shakhan, j'ai passé des années à explorer les quartiers, les restaurants et les événements culturels de Montréal, à partager des joyaux cachés et des expériences uniques avec les lecteurs. Je combine des aventures personnelles avec des conseils pratiques pour vous aider à profiter de la ville comme un local.
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