There are friends you meet who feel like they’ve been edited into your story, their presence so pivotal that you can hardly picture the plot without them. For me, that friend was Sam—a curly-haired chaos agent with a laugh that could bounce off canyons and a knack for asking the exact question I didn’t know I needed to answer. Sam didn’t just change my life; he flipped the script on so many things I thought I had figured out, including relationships, risk, and even the way I interpret a good sunset.

Here’s the thing about Sam: He was the kind of friend you’d want in your corner if life ever threw you into a poorly planned reality show. With him, you were guaranteed adventure, laughter, and—if I’m honest—a few moments of sheer panic. But looking back, some of the wildest roads we walked together, literally and metaphorically, are the ones that taught me what it means to truly connect with someone else.

The Birthday That Went Sideways and the Question That Broke Me Open

It started on my 25th birthday. The plan had been simple: a low-key hike to a hidden waterfall above Boulder, complete with trail snacks, maybe even a beer or two if we felt brave at altitude. But Sam, ever the benevolent agent of chaos, took “low-key” as a suggestion. Before I knew it, we’d veered off the intended trail, following his half-sketched map to what he swore would be “an epic viewpoint.” Several hours, one misplaced boot (his, not mine), and countless mosquito bites later, we found that viewpoint. It wasn’t epic, unless you count the view of our car far below in the distance—the size of a Matchbox toy.

Sam collapsed onto a boulder, pulled out two granola bars from his pocket, and said, “Hey, what’s the one thing you’re not doing in your life because you’re scared to fail?”

Cue the sound of my internal brakes screeching hard enough to wake the birds. I had expected a “Happy Birthday!” and maybe a toast with slightly warm water bottles, but not an existential challenge about all the ways I’d been playing small. Yet Sam was the kind of person who could lob a life-changing question like it was casual banter.

That day, we talked about everything I’d been side-stepping: friendships, ambitions, the way I’d been treating my relationships like plants I forgot to water. By the time we finally staggered back to the car—yes, shoeless Sam and I—it was clear that I was in the middle of one of those moments that shape you.

What Sam Taught Me About Being Real

Sam operated like a walking experiment in authenticity, filtered by zero self-doubt but a surprising amount of self-awareness. Here’s what I learned from him:

  1. Own the Mess
    Sam wasn’t afraid to say, “Yeah, I screwed that up.” Whether it was a failed climbing route or an awkward Tinder date where he quoted The Princess Bride verbatim (bad move, apparently), he refused to hide his messy moments. His transparency wasn’t just endearing; it was freeing. If he could own his goof-ups without apology, why couldn’t I?

  2. Ask Better Questions
    Long before I met Sam, I thought great conversations revolved around witty banter or impressively polished anecdotes. Sam taught me otherwise. He would ask things like, “What’s a decision you regret that you also absolutely wouldn’t take back?” or “Have you ever stared at something beautiful and felt small in a good way?” They weren’t questions you could answer on autopilot. And more importantly, they made you feel seen.

  3. Connect Without Keeping Score
    Keeping track of who reached out last or who “owed” who a favor didn’t exist with Sam. He believed relationships—whether platonic or romantic—weren’t transactional. This mindset shifted my own approach to connections. Instead of tallying effort, I began focusing on simply showing up.

Where This Story Meets You

At this point, you might be wondering: What does my mildly unhinged, sandal-losing friend have to do with your life? Here’s why Sam’s impact stuck with me: Whether you're looking for a partner, making friends as an adult (a Herculean feat, honestly), or just trying to deepen your existing relationships, the principles Sam lived by might shake things up for the better.

  • Be Curious: Instead of pummeling through small talk or replaying the same conversations like a broken playlist, find out what makes someone come alive. Ask the bold questions without worrying about coming off too “intense.”
  • Try Before You’re Ready: Yeah, you might look ridiculous, but most people are too busy wondering if they look ridiculous to notice. Sam never waited for the perfect moment, and frankly, it made things more interesting.
  • Celebrate the People Who Call You Out: Celebrate the Sams in your life. They’re the ones who’ll risk your brief discomfort to tell you what you really need to hear.

The Long Road Back to That Trail

The kicker? Sam and I eventually lost touch—one of those bittersweet twists you never see coming, but come to accept. I think about him often, especially when I’m hiking a questionable trail. I don’t know where he is now, and I have no doubts he’s out there, probably two hours into an unmarked trail with some poor unsuspecting soul in tow.

But the lessons he left behind are baked into how I approach just about everything. Sam taught me that connection, whether with friends or romantic partners, is rooted in showing up as yourself, flaws, mosquito bites, lost boots, and all.

Take a Risk

Here’s my takeaway for you: Be the kind of friend who can change someone’s life by challenging them, supporting them, or just showing up in the right way at the right time. And be the kind of friend who’s open to being changed, too. Your story—and your relationships—will be all the better for it.