The Stranger Who Taught Me a Lesson


It was a Tuesday morning. I remember because I spilled coffee on my hiking boots and muttered something unkind about “the universe conspiring” against me—not that the universe cares much about caffeine accidents. I was sitting in a café in Boulder, hunched over my journal, feeling absurdly introspective, when the stranger walked in. Or, more accurately, sauntered. The kind of person who exudes effortless calm, like a yoga instructor who secretly irons their sweatpants.

She asked to share my table, and I nodded, drowning in the obligatory awkwardness that comes with caffeine-fueled small talk. Little did I know that in the next hour, this woman—whose name I never even learned—would flip my entire perspective on relationships and life.


"Map Your Relationships Like a Trail"

The conversation began innocently enough—she complimented my scribbling, I mumbled something about journaling. Eventually, we found ourselves talking about hiking, which in Boulder is practically required by city ordinance. She pulled out a detailed trail map, edges frayed, and spread it across the table. It wasn’t just any map. It was a hand-drawn maze of trails from Utah’s Arches National Park, annotated with notes like “Lulu fell here, wine saved morale” and “Liz & Me: Serious Chat Spot.”

I asked about the notes, and she waved a dismissive hand, almost embarrassed. “It’s just my way of keeping track of people in my life,” she explained. Every note represented a memory shared with a friend, a hike taken with a partner, or a solitary trek that taught her more about herself.

Her metaphor was so simple, and yet it hit me harder than the iced Americano I’d just chugged: our relationships—romantic, platonic, familial—are like trails. Some are familiar loops you visit over and over, safety in predictability. Others are steep climbs with switchbacks that leave you gasping but exhilarated by the view. And then there are the dead ends—those paths you stumble down, only to realize they don’t lead anywhere. They’re frustrating, sure, but they still teach you something. Like how to navigate loss or how to recognize warning signs on trailheads (and Tinder profiles).


"Not Every Trail—or Person—Is Forever"

She said something that still gives me goosebumps: “Miles, we get so caught up in finding ‘The One.’ But humans aren’t meant to be destinations. They’re trailheads. Some lead to grandeur. Others? Just a quick stroll.”

It felt profound—an indie-folk-song-level epiphany—but looking back, it was just plain common sense. However, isn’t that the thing about common sense? It rarely feels profound until someone serves it with a side of vulnerability.

Her point wasn’t that we should give up on the idea of commitment, but that we need to reframe how we think about relationships that don’t last forever. A short hike isn’t a failure because it was short; it’s a success because you left with muddy boots, sore legs, or the realization that hiking in flip-flops is a rookie mistake.

We swapped hiking stories that mirrored our relationship histories. I confessed to a tendency to stick with bad trails (read: bad girlfriends) out of sheer stubbornness, internalizing every mosquito bite as endurance, every missed waymarker as proof of my loyalty. She laughed and said, “Your problem’s not the trail; it’s that you’re using the wrong map.”


"4 Relationship Lessons From the Backcountry"

Our conversation wasn’t just an exercise in metaphor. She left me with a practical—and surprisingly effective—framework for reframing relationships, and it’s too good not to share. Whether your journey has you bushwhacking through heartbreak or coasting down the path of a new romance, these lessons may come in handy:

  1. Judge the Trailhead, But Lace Up Anyway
    Look, not every connection screams “epic journey ahead.” Sometimes, the parking lot smells like hot asphalt, or you have doubts based on the Yelp rating (aren’t reviews just modern-day Greek oracles?). But you can’t really know unless you start the hike. Letting your guard down is the first step toward discovery.

  2. Don’t Race to the Summit
    Romantic comedies fool us into thinking all great love stories peak in two hours, but trails—and relationships—are unpredictable. Take your time. Snap a mental photo. Appreciate the wildflowers instead of worrying about what’s over the next ridge.

  3. Pack Snack Breaks
    In relationships, as in hiking, burnout is real. A pause to recharge—whether it’s a solo yoga session or a walk through your favorite park—doesn’t mean you’ve lost momentum. It just means you’re valuing yourself along the journey.

  4. Check Your Compass (a.k.a. Your Non-Negotiables)
    Backcountry trails aren’t safe if you forget a map, water, and common sense. In relationships, forgetting your boundaries, values, and emotional needs is equally reckless. Know your compass points and stick to them.


"Love Is For the Brave (and Perhaps the Foolishly Hopeful)"

Before she left, she leaned back in her chair, inspected me like a trail she wasn’t quite sure about, and tossed out her final piece of wisdom: “The best hikes are the ones where you embrace both the beauty and the bugs.”

A part of me wanted to ask if she was single, but something told me she was one of those people who was perpetually off the market—not because she was taken, but because she wasn’t interested in being boxed in by labels. Anyway, the moment wasn’t about romance. It was about growth.

She walked off, leaving me with a caffeine buzz, half a croissant, and the curveball realization that strangers sometimes feel like guides down paths we’re hesitant to explore. After spending years trying to “figure out” relationships, her advice boiled it all down for me. Stop trying to chart every unknown future. Instead, lace up, keep your map handy, and trust that the trail—no matter how rough—has something to teach you.

The coffee shop buzz returned to normal after she left, but I stayed a while longer. I pulled out my journal and scribbled one simple note about the day: Best coffee shop encounter ever. Lesson learned: Life isn’t about conquering trails; it’s about enjoying the hike.