There’s a story my dad used to tell on cold winter nights, the kind of nights when the wind howling through the cracks in the cabin walls sounded less like weather and more like wolves in mourning. We’d huddle around the wood-burning stove, its creaking warmth battling the Wyoming chill, and he’d start in with the same words every time: “Did I ever tell you boys about Uncle Roy and the diamond engagement ring?” Spoiler alert: he had—countless times. But no one stopped him. Family lore gets polished with each retelling, like good boots worn down by familiar trails.

Uncle Roy's tale wasn’t just a funny memory passed down over mugs of cocoa; it was a blueprint for understanding life, love, and the curious ways people go about chasing both. The lessons I learned from his story still shape how I approach relationships today—whether it’s flirting with someone new or finding steadiness with someone familiar.

The Proposal That Wasn’t

Uncle Roy, as my dad painted him, was big, boisterous, and about as subtle as a gun rack on a Prius. Born with a charm that mostly got him out of trouble, but not much further, he had a long history of falling hard and fast. Enter: Cynthia. She showed up from Chicago one summer to work at a dude ranch down the road. Cynthia was everything Roy wasn’t—polished, practical, and unimpressed by swagger. Naturally, Roy decided he was going to marry her.

Now, most people in sparsely-populated ranching country knew when to dial down the theatrics. Not Roy. Nope, he decided his best move was to buy a diamond engagement ring on credit he didn’t have. Mind you, this was the 1970s, when “you miss 100% of the shots you don’t take” wasn’t motivational office-wall decor; it was your uncle getting rejected in epic fashion.

The morning of the proposal, Roy packed the ring in his saddlebag and invited Cynthia for a ride up to a scenic overlook. But Cynthia, practical to her Prairie Core roots, opted to clean stalls instead. Unfazed, Roy pivoted to Plan B: proposing publicly at a local barn dance. That ring never made it out of his pocket. Cynthia, bless her, declined before he even had the chance—and not quietly. The entire barn apparently heard her, “You don’t LOVE me, Roy; you just like the IDEA of me!” Roy stumbled home that night, proposing instead to a bottle of bourbon.

The fallout from that ring became one of our family’s most enduring punchlines. It took him years to pay off the debt, and even longer to understand Cynthia’s parting shot wasn’t just criticism; it was truth. She liked him enough to be honest.

What Roy Taught Me About Authenticity

Uncle Roy’s story shaped my understanding of relationships long before I ever went on a first date. As a teenager, straddling the awkward slog of figuring out emotions (and hormones), the lesson of Cynthia’s rejection started to crystallize: there’s no point pretending to be something you’re not. That ring represented effort, sure, but it also symbolized Roy trying too hard to make his feelings fit into her reality. She saw through it, and rightly called him out.

Authenticity matters in relationships—not just because it makes it easier to connect with others but because it saves you from spinning your own wheels. Trying to fit your personality into someone else’s idea of what a “perfect partner” should look like? That can only hold up for so long. Like a cheap barn repair after a storm, cracks will show.

The Family Tradition of “Big Swings”

If there’s any Harcourt tendency that’s all but written in our DNA, it’s the "Big Swing." Uncle Roy wasn’t the first or last character in my family to concoct a wild plan fueled by optimism and poorly-timed budgeting. One summer, my brother tried to impress a girl by teaching himself to play the banjo (spoiler: it worked, but only because she had somehow never heard a tuned banjo before). When I was 22, I made my own Big Swing, scrapping together savings to fly to New Zealand in some harebrained scheme of eco-volunteering and soul-searching, only to get dumped right before I went. Family tradition, I guess.

The difference is, over time, I’ve come to appreciate the balance between grand gestures and grounding yourself in what’s real. Flirtations and passion have a place—and thank goodness for them—but if they don’t grow from genuine intentions, you end up holding promises you can’t keep.

Flirting vs. Futures: Know the Difference

So, what do you do with this kind of family folklore? Besides sharing it with strangers on the internet, I mean? Turns out, Uncle Roy’s diamond debacle left me with some practical takeaways for navigating the trickier intersections of flirtation and relationship-building.

1. Feelings Are Valid, but Not Always Logical

Emotions, like Wyoming weather, are unpredictable. Feel them fully, but don’t mistake grand declarations for a foundation. If you’re rushing headlong into something, ask yourself first: is this about the person or the idea of the person?

2. Be Honest About What You Want

Cynthia’s takedown was brutal but fair. She set a boundary instead of leading Roy on. The more honest you are—early and often—the fewer half-written proposals you’ll need to take back later.

3. Exaggerated Gestures Are Overrated

Romcoms sold us a false bill of goods. You don’t need to flash mob someone’s front yard, quit your job for love, or, in Roy’s case, buy a diamond ring with money you don’t have. Subtle gestures rooted in intentionality almost always land better. Trust me, the bouquet of hand-picked wildflowers beats a credit-card bouquet any day.

The Power of Owning Your Stories

The beauty of family lore like Roy’s isn’t just in the humor of it—though, let’s be honest, the image of a cowboy sulking into a bottle of Jack remains delightful. These stories become roadmaps for navigating our own messes with a little more grace. Sure, Roy might not have gotten Cynthia, but he got something better: clarity, humility, and maybe a better interest rate on his next credit card.

As for me, every time I think about Uncle Roy, I roll my eyes and laugh—because let’s face it, there’s probably at least one ring-sized mistake in every family tree. But I also stop to check myself. Am I being genuine? Am I keeping my foot out of Uncle Roy territory? If not, well, chances are I’m headed for a story-worthy moment of my own.

So gather your stories. Tell them often. And next time someone brings up a grand gesture, think of my family’s long history of Big Swings. They don’t always land, but they always teach—and they always leave you with a funny tale for the campfire.