When Your Family Drama Sounds Like a Country Song

Growing up on a ranch in Telluride, Colorado, meant my childhood was a lot of dirt roads, open skies, and family stories that could rival any Netflix drama. No lie, I once described my family to a friend as “a little bit ‘Yellowstone,’ but with less cattle and more passive-aggressive casserole sharing.” Every family has its lore, those stories passed down that shape how we see the world, love, and sometimes, whether or not we trust people who chew gum too loudly (more on that later).

When I think about my own relationships—romantic or otherwise—I can’t ignore the fact that these stories played a huge role. Some taught me resilience, others gave me a good reason to move 500 miles from my closest relative. Either way, they all left their mark. And lucky for you, dear reader, I’m going to share a few of the hits.

The Tale of the Horse Named Trouble

My dad loved to tell the story of Trouble, a sorrel mare with a knack for escape that bordered on Houdini-level genius. Trouble didn’t just jump fences; she evaluated them for structural weaknesses. She also had a bad habit of leading other horses—our actual income source—on breakout missions.

One summer, after she broke out for the third time in a week, my dad’s patience finally hit its limit. He declared (loud enough for the mountains to hear), “That horse is more trouble than she’s worth!” Thus, the mare earned her name.

When I was about 14, I got it into my head that I could train Trouble. I spent weeks coaxing her into trusting me. My secret? A pocket full of carrot chunks and an unrelenting belief that I could charm my way through anything (a theme that would later extend to my teen dating life, with slightly less success). But here’s the kicker: Trouble never stopped being Trouble. She’d behave perfectly until the second you let your guard down, and then bam! She’d step on your foot or dump you in a creek.

That horse taught me two invaluable lessons:
1. Pay attention to patterns. Whether it’s horses or people, sometimes what they show you is who they truly are.
2. Charm alone isn’t enough. Sure, it’s nice to be liked, but respect and consistency do way more heavy lifting in relationships.

Aunt Judy’s Dating Rules (and the Gum Incident)

Every family has an Aunt Judy. She’s the one that tells it like it is, unfiltered, while wielding a martini glass in one hand and a deviled egg in the other. Aunt Judy was a serial dater—a widow twice over and deeply suspicious of any man under six feet tall. She wasn’t bitter, she was experienced.

Her iconic advice included:
- "Never trust a man who won’t eat pie. It’s unnatural.”
- "If he’s not making you laugh, what’s the point?"
- And my personal favorite: "Run, don’t walk, from someone who chews gum loudly—it’s a sign of poor self-control."

Now, as absurd as some of this sounds, Aunt Judy’s words stick. Her pie rule? It’s less about dessert compatibility (thankfully) and more about finding joy in the simple pleasures of life. Her humor test? Pure gold—because let’s face it, being able to laugh together might just be the bedrock of a lasting partnership. As for the gum thing... well, let’s just chalk that up to personal preference.

When I eventually started dating seriously, I realized how much Aunt Judy’s advice had seeped into my psyche. I even caught myself internally judging one guy for turning down a perfectly good slice of peach cobbler. (Reader, it did not work out.)

Grandpa’s Great Mountain Proposal

Every romantic in my family eventually comes back to Grandpa’s proposal story. According to family lore, he proposed to my grandma while they were perched on a boulder halfway up a mountain trail. The way he told it, he’d been planning some grand speech, but when the moment arrived, he got so nervous that he blurted out, “Wanna do this forever?” She laughed so hard she nearly rolled back down the trail, but she said yes.

I think about that story a lot—how what might seem like a clumsy moment became the foundation of a 50-year marriage. It’s a reminder that love isn’t perfect words or elaborate plans; it’s the effort, the sincerity, and yes, even the slightly awkward delivery.

After hearing that story a hundred times over, it’s impossible not to root for the kind of love that feels real and grounded and maybe a little messy.

What My Family Stories Taught Me About Connection

Here’s the thing about family stories: They stick to your ribs like biscuits and gravy, whether you want them to or not. But if we listen closely, they also have a way of handing us little roadmaps, especially when it comes to navigating relationships.

Here are a few lessons I’ve picked up along the way:

  • Know Your Patterns: People are creatures of habit. Pay attention to behavior—yours and theirs. If someone (or some horse) keeps doing the same thing, stop expecting a different outcome.
  • Find Someone Who Makes You Laugh: Bonus points if they reach for the pie without hesitation.
  • Embrace Imperfection: The best love stories aren’t flawless; they’re honest and full of heart.

Wrapping It All Up

Not all family stories are picture perfect. Some are the kind you pull out at dinner parties for laughs; others may require side therapy sessions. But at the end of the day, they shape us. They teach us what to look for, what to watch out for, and sometimes, to just laugh at the chaos.

So the next time you find yourself sitting across from someone on a date, debating whether they’ll pass the pie test, just remember this: Every love story starts with a question. It doesn’t have to be a perfect one—it just has to be honest.

Now go out there and write your own lore—just maybe leave the loud gum chewing and creek-dumping horses out of it. You’ve got this.