There’s something humbling about the moment when a grand plan—one you were sure would go down in your personal history as a stroke of genius—falls apart at the seams. Mine involved a girl, a picnic basket, and an overly ambitious horse named Dakota. But let me back up and paint you a picture of what should have been the most romantic day of my life. Spoiler alert: It wasn’t.
The Grand Romantic Gesture That Wasn’t
It was late summer in Telluride, that golden window of perfect weather before the aspens turned. Mountains stretched endlessly, blue skies rolled out like a welcome mat—it was the kind of backdrop that begged for a love story. I’d been dating Hannah, a fellow history nerd I’d met at a living history reenactment (nothing says chemistry like shared enthusiasm for 19th-century mining tools). Things were getting serious, and I wanted to show her the kind of place that shaped me—the wide-open trails, the high country views, the smell of sagebrush after a rainstorm.
So, naturally, I decided that a sunset horseback ride followed by a secluded picnic would be the move. Sweeping vistas, a homemade charcuterie spread tucked in a vintage wicker basket, and Dakota—our family’s most photogenic gelding, beloved by honeymooning tourists—was to lead the charge. I had it all planned: the ride would be smooth, the food delicious, and, if things went really well, there’d be a moment where we’d lock eyes as the sun dipped behind the mountains. Tom Hanks wouldn’t have stood a chance against me in the Rom-Com Olympics.
The execution, though? Let’s just say Dakota didn’t read the same script I did.
When the Horse Decides It’s His Story
Things started unraveling about twenty minutes into the ride. Dakota, usually calm and reliable, had apparently decided today was the day he’d audition for the rodeo. My theory? He caught wind of my nervous energy and decided the broody mountain cowboy act wasn’t cutting it.
Hannah, to her credit, was a champ. She laughed off Dakota’s attempts to speed up the trail at 15 mph, as I tried to maintain composure by shouting phrases like, “He’s...uh...spirited today!” Translation: I have zero control over this situation, and I hope you don’t notice.
By the time we reached the designated “scenic spot,” my confidence had already taken a beating. I tied Dakota to a nearby tree and tried to salvage the mood by pulling out the picnic basket. Very suave, I thought. Except...the basket smelled funny. Not just funny—rancid. Turns out I’d misjudged how long cheese could survive in a hot car in a mountain town. The brie had become a biohazard.
Hannah gamely nibbled on some crackers (bless her), but I could see things were falling apart. I gave a half-hearted joke about rustic life being unpredictable and popped the cork on a bottle of wine. That’s when Dakota, clearly bored with the whole setup, yanked the lead rope loose from the tree and took off running. With the wine.
Lessons in Letting Go of Perfection
There’s a moment in every good disaster where you realize you’ve lost total control. Watching Dakota gallop into the wilderness with my $30 Merlot swinging from the saddle horn was that moment for me. I jumped up to chase him, leaving Hannah sitting there, likely wondering how she’d ended up on this episode of "Colorado’s Worst First Dates."
Eventually, I managed to wrangle Dakota, but the wine was gone, shattered somewhere on the rocky trail. Sticky purple stains covered the saddlebag like some kind of crime scene. By the time I returned to Hannah, sweaty and embarrassed, the romance had left the building.
“Let’s just enjoy the view,” she said. No judgment, no sarcasm. Just...kindness. That’s when it hit me: I’d been so focused on orchestrating the perfect romantic gesture, I’d forgotten the reason behind it. Hannah didn’t care about the sunset horseback ride or the gourmet cheese plate or the fancy wine (OK, maybe she cared a little about the wine). She just wanted to spend time together.
Four Takeaways from My Biggest Misadventure
In hindsight, I learned more from that picnic-that-wasn’t than I have from any “10 Ways to Be Romantic” list you’ll find online. Here are the lessons I took away—and no, they don’t involve rethinking my love for horses:
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Effort Trumps Perfection Every Time
No one’s expecting sweeping cinematic romance at every turn. What matters is showing that you care enough to try. It’s easy to forget that little imperfections can make the experience more memorable (and funny) in the long run. -
Know Your Battlefield (or Trailhead)
A romantic gesture works best when tailored to your audience. Would Hannah have been just as happy with a hike and sandwiches we didn't have to refrigerate? Probably. I should’ve leaned into simplicity—she never asked for a production. -
Don’t Let Ego Ride the Horse
I went into this thinking I’d impress her to the point of applause. But relationships aren’t performances. They’re about connection, and showing up authentically beats pulling off a stunt any day. -
Learn to Laugh at the Chaos
If you can find humor in the moment (even when it feels like a disaster), you’re golden. Hannah not only stuck it out but later admitted watching Dakota bolt with the wine was one of her favorite memories of the day. Why? Because it was real.
Trailblazing Toward Self-Discovery
That day didn’t end the way I imagined, but in a strange way, it was better for it. I learned that the best romantic gestures aren’t about the perfect backdrop or the flawless execution—they’re about vulnerability. About saying, “Hey, I’m trying here,” and letting the other person see behind the curtain.
Hannah and I didn’t end up riding off into the proverbial sunset forever; life took us in different directions. But even now, I carry that misadventure with me like an old scar—a little cringe-worthy, sure, but uniquely mine.
So, the next time you’re planning a big romantic gesture or trying to orchestrate the perfect date, remember this: the goal isn’t to impress but to connect. And if things go a bit sideways, like they did for me, embrace it. What’s more romantic than showing up as you are, wine-stained saddlebags and all?
