We all have those moments when we look back and think, “If only I’d known then what I know now.” Like the time I wore cowboy boots to run a 5K (spoiler: don’t), or the year I thought the key to winning someone’s heart was learning to juggle (again, don’t). Life, much like dating, has a funny way of teaching us lessons the hard way. And let me tell you, I learned some of those lessons riding through the peaks and valleys of life—and love. Here are a few nuggets of wisdom I wish someone had handed me sooner, preferably scribbled on the back of a bar napkin.

1. If You’re Trying Too Hard to Impress, You’ll Miss the View

Growing up on a ranch, I always wanted to be the guy who knew the land better than anyone—the one with the coolest stories around the campfire. Sounds romantic, right? Except there was the time I took a date on what I thought was a “breathtakingly scenic” horseback ride and ended up getting us lost in a snowstorm. My date? She wasn’t impressed—she was freezing.

Turns out, people aren’t charmed by grandiosity or antics that scream, “See how cool I am!” What matters? Showing up as yourself. Not a shinier version of yourself. Not someone who seems like they wandered off a motivational Instagram post. Just you. Whether you’re navigating a date or introducing someone to your quirks (hello, my love of collecting Civil War-era buttons), authenticity is always the best compass.

2. Overthinking Is the Enemy of Connection

Let’s talk about the “three-day rule,” the “don’t respond to texts too fast” rule, and every other ridiculous dating guideline straight out of a rom-com. Those rules are about as useful as wearing spurs to a coffee shop—utterly unnecessary and utterly annoying to everyone involved.

Years ago, I was on a date with someone who made me laugh so hard, I accidentally spilled my water all over myself. In my mind, I thought, “Game over, McAllister, you’ve blown it.” But instead, she cracked a joke about us being an actual trainwreck and ordered refills. We ended up having the best time because we stopped taking the night so seriously.

Pro tip: The less time you spend scripting the perfect line or calculating your “next move,” the more time you actually have to enjoy getting to know someone. Life is messy. Laugh about it.

3. Red Flags Are Not “Creative Challenges”

Confession time: I’ve been guilty of the ol’ “maybe I can fix them” mindset. Dating someone who broods beautifully or has a laundry list of commitment issues might sound dramatic and exciting—at first. (Anyone else binge-watch a few too many ‘90s teen dramas?) But trust me, it’s a bit like trying to hike a steep trail after ignoring a “Do Not Enter” sign. The warning was there for a reason.

Here’s the hard truth: you can’t bend over backward enough to “fix” someone who doesn’t want to fix themselves. Focus instead on finding someone who’s willing to meet you halfway, not someone who treats emotional growth like optional flossing. Respect yourself enough to value mutual effort—and healthy boundaries.

4. The Little Things Matter—A Lot

In Telluride, the saying goes, “It’s not just about the summit; it’s about the steps that get you there.” The same principle applies to relationships. Grand gestures might make for entertaining stories (looking at you, guy with the flash mob proposal), but they aren’t what make two people stick together.

It’s the little things. Like remembering how someone takes their morning coffee. Or texting “good luck” before they give a big work presentation without being asked. One of the most meaningful moments I ever shared with a partner wasn’t during a fancy vacation—it was sitting on the tailgate of my truck, watching the stars above the Rockies while sharing a bag of stale popcorn.

It’s easy to forget that solid relationships are built on thousands of tiny, thoughtful moments. So, don’t overthink showing you care. Gratitude and attention always go further than you think.

5. Silence Isn’t Always Awkward

When I first started dating, I treated every lull in conversation like an emergency that needed fixing immediately. (Quick: Say something poetic! Ask about their weirdest childhood dream!) But what I’ve come to realize—on a ranch trail, under a quiet sky—is that silence can be not only comfortable but necessary.

We live in a world that never stops buzzing, pinging, and notifying. A moment of pause, when you don’t have to fill the space with words, is rare—and deeply telling. Can you sit in silence with someone and still feel at ease? That’s intimacy.

The next time you’re on a date and experience an awkward pause, embrace it. Don’t overcompensate. Sometimes the greatest connections settle into your life softly when you both take a breath and simply exist.

6. Don’t Forget to Date Yourself, Too

One of the best pieces of advice I’ve picked up is this: If you don’t know how to enjoy your own company, it’s going to be awfully hard to let someone else in. Growing up in Telluride taught me how to appreciate solitude. Whether it was exploring the vast mountain trails or spending hours immersed in writing, I realized early on that being alone isn’t the same thing as being lonely.

Get out there and pursue the things that bring you joy, not just the things that might impress someone else. Whether that’s taking pottery classes, mastering the fine art of sourdough baking, or finally learning Willie Nelson’s “Blue Eyes Crying in the Rain” on guitar—pour into your own cup. When you fill yourself up, you show up in relationships feeling whole, not waiting for someone else to do the filling for you.

7. Vulnerability Is the Real Deal Closer

Here’s the truth dating apps don’t tell you: the polished, curated version of yourself might get a few swipes, but vulnerability is what leads to connection. Relationships—whether fleeting or forever—aren’t forged in perfection; they’re shaped by shared truths.

Let me tell you about the moment I decided to stop dodging vulnerability. I was dating someone who asked about my childhood, and instead of offering the usual, surface-level story about my “idyllic ranch life,” I told her the truth: I missed out on a lot of carefree kid stuff because I was helping run my family’s struggling business and feeling the weight of it. That conversation opened a door to real connection, one that never would’ve existed otherwise.

So, yes, let people see your rough edges. Talk about your fears as much as your dreams. Vulnerability doesn’t scare off the right people—it draws them in.

Final Thoughts: Keep Riding the Trail

The thing about life—and dating—is that none of us have it all figured out. We’re all just riders on this dusty, unpredictable trail, learning as we go, sometimes the hard way. And that’s okay. Every romantic misstep, every cringe-worthy date, and every laugh-out-loud “what-was-I-thinking” moment help shape who we become.

So, the next time you catch yourself wishing you’d done things differently, remember this: Every stumble along the way is part of the story you’re writing. Be kind to yourself (and others) out there. As the saying goes in my neck of the woods, “The view’s just as beautiful from the bumpy paths—you just have to hold on.”