If you’ve ever tried to plan the perfect romantic gesture only to watch it crumble faster than a dry slice of cake at a backyard wedding, then you, my friend, will probably find solace in my story. Spoiler alert: it features me, two train tickets, and a grand idea gone hilariously—then humblingly—wrong. Because nothing says romance like learning that sometimes, the ride is bumpier than you expect.
The Plan: Paris Without the Plane
A few years ago, after spending a brief but formative stint in London, I decided to bring some of that European charm back to Toronto. My then-girlfriend, let’s call her Sophie (because no one ever uses names like Irene for these stories), was a hopeless Francophile. She loved croissants without butter guilt, had reread A Moveable Feast more times than I had rejected writing deadlines, and even owned a beret, ironically, she claimed. So for her birthday, I decided she deserved something a little magical.
But flying her to Paris wasn’t an option—because I was a writer, and Air Canada doesn’t take “exposure” as payment. Instead, I landed on the next best thing: Montréal. It was just a train ride away, bilingual, and French(ish) enough to deliver the charm while respecting my post-liberal-arts-budget constraints. With the kind of optimism only possessed by people who still think logistics should take a backseat to vibes, I booked the train tickets and planned an entire weekend of wine, poutine, and cobblestone strolling.
My pitch to her was simple but bold: “Pack a bag. Think Paris—without the existential dread.”
The Journey: A Series of Unfortunate Events
The first crack in my shiny plan appeared when we arrived at Union Station. The train I had booked—along with three others that morning—was delayed. First by 20 minutes, then an hour, then “until further notice.” VIA Rail blamed the weather, which, in Canada-speak, could mean anything from light drizzle to spontaneous polar vortex.
Sophie, to her credit, handled the delay like a champ, joking that at least we were getting the authentic train experience—translation: discomfort, zero snacks, and mysterious smells. But by the time we finally boarded, well past noon, her enthusiasm had started to resemble that one leftover croissant no one wants at the work potluck—stale and a little squashed.
Pro tip: There’s no faster way to test your romantic compatibility than being stuck for six hours in a moving steel box where the Wi-Fi is slower than a toddler learning cursive. By the time we reached Montréal in the late evening, all ideas of strolling through Old Port with gelatos had been traded for frantically Googling which restaurants were still open. Answer: none, unless we wanted an artisanal hot dog at the 24-hour depanneur. Bon appétit?
The Execution: French Flop, Canadian Edition
The next morning, I was determined to salvage the weekend. I picked a cozy little café in Plateau Mont-Royal for breakfast. By “picked,” I mean I scrolled through Yelp and went with the highest-rated option that didn’t mention “fusion.” To my credit, I nailed the vibe: it had chalkboard menus, exposed brick, and servers who casually switched between French and English without making me feel like I was failing high school language class all over again.
Feeling like I was on a roll, I suggested we rent bikes and explore the city. Très romantique, right? Well, in theory. What I hadn’t factored in was Sophie’s aforementioned love for croissants and how it didn’t extend to cardio. Twenty minutes into cycling up some aggressively steep Montreal streets, she mutinied. Imagine a very polite but firm “Non, merci,” and then picture me doing a solo bike ride while she Ubered to our next destination. Not my proudest moment.
The low point of the trip came later that evening when I, in a burst of misguided spontaneity, ordered us two glasses of wine at a fancy restaurant without checking the price. Of course, they arrived in thimbles. Sophie laughed—sort of—but I knew what that meant. No one in human history has laughed at a five-ounce pour of Pinot Noir and thought, “What a bargain.”
The Lesson: Perfection Is Overrated
By the time we got back to Toronto, I had expected Sophie to be politely furious—a Canadian specialty. But instead, she surprised me. “That trip was kind of a disaster,” she said with a smile, “but…it was still fun. In a weird, ridiculous way.”
And that’s the thing. Not every relationship has to run like a romantic comedy where the protagonist gets everything pitch-perfect. Sometimes it’s more like an indie film—awkward conversations, botched plans, questionable cinematography, but a whole lot of heart.
Looking back, I learned three important lessons that weekend:
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Overthinking Spontaneity Defeats the Purpose
If you’re doing something spontaneous, like planning a romantic getaway, keep it simple. The moment I started layering in surprise wine bars and bikes that required unearned quadriceps strength, I pretty much doomed myself. -
It’s Okay to Laugh at the Messiness
Travel delays and overpriced wine aren’t romantic in the traditional sense, but the ability to laugh your way through them? That’s a sign you’re building something real. Like, “We survived this mess, so a clogged kitchen sink is child’s play” kind of real. -
Don’t Confuse Grandeur with Meaningfulness
Instead of trying to approximate Paris, I could’ve just leaned into Montreal for what it is—a city with a unique (read: cost-efficient) charm. Romance doesn’t always need to look Pinterest-worthy. Bringing genuine effort and thoughtfulness will get way further than theatrics, trust me.
The Takeaway: It’s About the Connection
Not every date or weekend away has to impress like a Ted Talk. Much of the energy we waste trying to make things perfect could be better spent immersing ourselves in the people we’re with. Sophie and I didn’t last forever, but even now, I remember that trip in flashes: us huddled together at a train platform sipping burnt coffee, laughing over greasy poutine, and trying (unsuccessfully) to take a cute selfie in subzero winds.
And isn’t that the whole point? Romance isn’t about creating a fantasy. It’s about finding joy, humor, and connection in the reality—even when it’s delayed, awkward, or riding a rental bike uphill.
