It was a cool October evening when I found myself hiking into the radiant high desert around Santa Fe, a bouquet of sunflowers clutched in my hand and an overcooked plan tucked firmly under my arm. The sun was dipping low, stretching shadows over a landscape so quintessentially New Mexico it could’ve been mistaken for the backdrop of an O’Keeffe painting. I had a grand idea: I was going to confess my feelings to a guy I’d spent months quietly falling for, and I was going to do it creatively. Not with a dinner date or a breezy text but with a full-blown art-inspired gesture. A love confession worthy of...well, a rom-com or at least the Pinterest board I’d pieced together like an amateur set designer. Let me tell you now: this did not go the way it does in the movies.

But first, let me set the stage—because context is everything when you’re about to narrate falling spectacularly on your face.

Big Feelings, Bigger (Over)Planning

His name was Clay (yes, really—foreshadowing in its purest form), and I’d first met him at a mutual friend’s gallery opening. He was tall, soft-spoken, and thoughtful in a way that made him stand out in a room of cocktail-sipping creatives. He had that archetypal Santa Fe vibe: someone who could lead a meditation circle at 6 a.m. and then offer surprisingly sharp insight into outsider art over lunch. We’d run into each other a few times after that, at flamenco shows, local markets, and even a storytelling night where he told a story about toppling his dad’s kiln as a kid. Somewhere between his lopsided smile and his awkward but charming hand gestures, I started imagining what it would be like if there was an us.

One evening over drinks—after my third margarita and far too much encouragement from my best friend—I decided I was tired of daydreaming. It was time to do something bold and totally unforgettable. Typical me, with my fine arts background, “bold” translated to performance-adjacent romantic stunts. Not candles and string lights but something grand, personal, and possibly involving props.

So, I dreamed up The Plan: I’d paint a landscape inspired by our early conversations, take him up to a beautiful overlook just outside the city, and surprise him with the painting and my sunflower-laden declaration. It felt poetic and impossibly romantic. The desert sunset, the breeze blowing gently as I handed him my creation, a soundtrack of coyotes howling in the distance—it seemed flawless in my head. Naturally, I ignored every voice of reason that suggested I might be overcomplicating things.

When Plans Meet Real Life

Cut to the big night: I picked an overlook just past Canyon Road, one of Santa Fe’s most picturesque art districts. I packed some snacks, wine (duh), and the aforementioned bouquet, already wilting inconveniently from my overzealous schedule. I texted Clay to meet me there for a surprise I promised would “blow his mind.” (Honestly, who says that? Past me, apparently.)

Things started going wrong roughly twelve minutes into our “perfect evening.” For one, I hadn’t checked the weather forecast, and what had been a clear evening turned cold and windy real fast. The view that had seemed majestic now came with the distinct scent of dirt flying directly into my mouth. Clay arrived—on time, because he’s an organized human being—and immediately asked if we were going for a hike.

“Nope! Just trust me!” I chirped, clutching my bag of romantic supplies as we continued toward the overlook.

The reveal—if that could even be the right word—was chaotic at best. I pulled out the painting, a deeply sentimental rendering of the Sangre de Cristo Mountains, full of moody purples and soft grays, meant to symbolize my feelings (shocker: visual metaphors aren’t always event-friendly). The problem? Even wrapped tightly, the wind had smeared one corner of the canvas. Part of the mountain now looked suspiciously like a blob.

“I painted this…um, for you,” I stammered as the sunflowers tried to escape my grasp. “And, uh, I wanted to tell you that I like you. A lot.”

Cue: deafening silence.

Clay stood there, visibly unsure what to say, arms awkwardly pinned to his sides like a marionette with tangled strings. Eventually, he muttered, “Wow, I didn’t expect this, um, tonight.” And the phrase I’ll never forget: “This is…very thoughtful.”

Let’s pause for a second here. If you’re ever in a situation where someone describes your romantic gesture as “thoughtful” and only thoughtful, it’s time to back away slowly and pretend the moment didn’t exist. But did I take the cue? Oh no. Like a protagonist intent on spiraling further, I started rambling—about the art, the symbolism, even coyotes—which only made Clay look more like he wanted to not be there.

By the end of the night, there were no coyotes, no confessions of mutual affection, and no Hollywood happy ending. There were two people shivering while packing up an ill-conceived art display and a very unromantic side hug before he left.

Lessons Learned (Painfully)

Here’s the thing about big romantic gestures—they work great if they’re built on a foundation of mutual understanding. But if you’re not already on the same page (or even in the same chapter), they can come off as overwhelming or even misaligned to the other person’s comfort zone. Looking back, there are a few takeaways from this misadventure that apply far beyond overzealous confessionals in desert winds.

  • Check your expectations: Did I confuse Clay being polite and lovely with him secretly harboring the same feelings I had? Absolutely. It’s important to check in with reality instead of projecting your hopes onto someone else.
  • Match your ambition to the relationship’s stage: Our connection was still casual and developing. My grand gesture probably landed like handing someone a three-tiered cake when all they ordered was a cupcake. Go for thoughtful but approachable, not overwhelming.
  • Timing matters (so does the wind): Emotions are best served with a side of awareness. Consider the setting, the vibe, and, please, check the weather if you’re planning something outdoors.
  • Keep communication simple: Sometimes, vulnerability doesn’t need to be wrapped up in metaphors and props. A heartfelt, straightforward expression often lands better than an elaborate one.

From Misadventure to Inner Peace

Clay and I didn’t go out again after that night—not because the over-the-top-romantic move doomed us, but because we really weren’t on the same wavelength to begin with. And that’s okay. My once-overwhelming embarrassment has morphed into quiet gratitude. That moment taught me more about staying present, respecting pace, and approaching romance with a healthy mix of boldness and self-awareness.

That painting is now hanging in my family’s gallery, by the way. Framed in worn wood and titled “What Was I Thinking.” People love it—sometimes mistakes make for the best stories and the best art.

If you’re on a romantic adventure and considering pulling off a grand plan, hold space to laugh at yourself if it doesn’t land perfectly. Take it from me: it’s often the unpredictable detours that teach us what matters most. Go big if you feel it, sure—but don’t forget to go real.