Some friendships are like a lightning strike—sudden, unexpected, and impossible to ignore. For me, that lightning struck the dusty floor of a community center gym in a tiny West Virginia coal town. It was here, over a borderline-dangerous plate of deviled eggs at a potluck, that I met Dean.

To this day, I can’t think about Dean without smiling, because he taught me one of life’s greatest lessons: how to laugh at myself and, by extension, how to love myself. Before Dean, I never fully realized how tied those two things were. And honestly, how could I? Growing up in a world of hardworking folks who measured worth by calluses on their hands made good humor feel like a luxury, not a necessity. But out of nowhere came Dean, shaking up my worldview the way Dolly Parton shakes up a room—loud, warm, and utterly unrepentant.

The Day We Met: A Masterclass in Charm

I remember it vividly. I’d just finished a lightning-fast “hello” speech, the kind you make when you’re the new kid in town. Having recently returned from grad school in California, I was a fish out of water—half mountain grit, half city pretension. And let me tell you, that’s a tough act to sell in Appalachia. Somewhere between listing my cultural history degree and joking that I once saw Leonardo DiCaprio at a café, I felt the crowd’s focus taper off like a disinterested date during a bad knock-knock joke.

That’s when Dean arrived, with his crooked smile and his absolutely flawless—or atrocious, depending on perspective—Hawaiian shirt. "Hey," he said, handing me a second deviled egg (was it planned? I’ll never know). "You look like you haven’t had a good laugh in a while. You ever play cornhole, college boy?"

Dean wasn’t just the guy who got me to play my first round of a backyard party game typically reserved for tailgates—he was the guy who made me laugh so hard mid-throw that I somehow nailed a perfect toss. He turned casual moments into comedy sketches. From then on, he became my unofficial guide to not taking myself so seriously.

The Wisdom of Humor: Lessons I Never Saw Coming

Lesson One: Flaws are Fun
Dean introduced me to the charm of imperfection. See, I’ve always been a bit tightly wound—fixating on doing things “right.” Whether it was writing research papers for professors in Berkeley or navigating first dates with precision akin to assembling IKEA furniture, perfection was my north star. And spoiler alert: that kind of uptightness can make you insufferable.

Dean, however, didn’t believe in polish. One summer evening, when a messy round of karaoke saw me squeak out a horrendous falsetto trying to slay Queen’s Don’t Stop Me Now, I felt almost paralyzed by embarrassment. “That was ugly as sin,” Dean howled after my performance. But, miraculously, he added: “But you know what? That made it twice as good!”

He taught me that the things we’re most afraid to reveal—our cringe-worthy, clumsy, monumental screw-ups—are often the quickest ways into someone’s heart.

The Power of Showing Up With Love

Lesson Two: Love People Where They Are
Dean never asked anyone to change. I once saw him invite a guy who’d just spilled an entire tray of Mountain Dew on Dean's favorite sneakers to sit down for a chat about 90s country music as if nothing had happened. “If I can still rock these kicks, they’ve got character now,” he laughed, already mopping them off with a paper towel.

It hit me then: Dean’s default mode wasn’t judgment—it was love. Now, I’ll admit, I wasn’t always great at taking this into relationships romantically or otherwise. Years later, during a messy breakup, I heard his voice in the back of my mind. “James, you can’t ask people for what they haven’t got.” That line stayed with me. Relationships, like friendships, survive on accepting each other’s flaws, failures, and damage.

Growth by Proxy: Dean’s Unexpected Talent for Matchmaking

Here’s a fun, cinematic twist: Dean inadvertently set me on the path to better dating. He wasn’t matchmaking in the traditional sense—you know, with setup dinners or awkward nudging toward someone across the room. Instead, Dean taught me how to be better at me.

There was this moment one autumn, sitting on the porch with him after some small-town bar crawl. Watching the fog roll through the hills, he blurted out the kind of advice that crawls into your head and lodges itself forever: “You’re way more interesting than you think you are. Stop trying to resize what you are for somebody else.” At the time, I laughed, called him Oprah, and opened another beer.

But dang it if he wasn’t right. Dean’s words coached me on every form of connection—from texting crushes in California to learning how to have deeper conversations with family. Each time, it came back to what he showed me: showing up honestly, unapologetically, and with a dose of humor changes everything.

Fearless Authenticity: What Dean Taught Me About Myself

When I imagine the way Dean moved through life, I think of John Bender in The Breakfast Club crossed with the wholesome chaos of Robin Williams’ Mrs. Doubtfire. He carried enough charisma and chaos to command the room, but just enough substance to make you realize there was something genius behind it all.

Dean’s humor wasn’t just something to laugh with—it was something to learn from. He had this way of showing that the more you embrace yourself, quirks and all, the more magnetic you become. And that’s not just about dating—it’s about human connection.

A Life Well-Lived, and a Legacy Left Behind

I’d be lying if I said writing about Dean wasn’t bittersweet. As larger-than-life as he was, his years were too short. Life got in the way—the way life does. He passed unexpectedly several years ago, but what he left behind wasn’t sadness. It was laughter, warmth, and lessons I carry daily.

I think about Dean when I fumble through my most awkward moments. I think about him on days when I feel a little lost, unsure of where I’m headed, or who I’m becoming. He’s the voice reminding me to lighten up, go easy, laugh loud, and love honestly.

Closing Thoughts: Be the Kind of Friend Dean Was

Summing someone like Dean up in one article feels impossible, but maybe that’s the point. He was a reminder that good friendships shouldn’t just be remembered—they should be learned from. So here’s the takeaway:

  • Laugh at yourself. Often, and unapologetically.
  • Love people where they are, messy and all.
  • Show up to life the way Dean showed up to his Hawaiian shirts—boldly and without apologies.

And maybe, just maybe, when you do, you’ll discover not only the joy of a perfect cornhole toss but the beauty of a life that’s unapologetically, gloriously yours.