No one tells you that hiking with strangers starts with a very specific kind of social theatre. You arrive early, pretend you’re not scanning everyone’s shoes, and silently deciding who looks like they know what they’re doing. There’s always that one moment where you wonder, did I pack enough water… or too much personality?
The greetings are polite but cautious. Everyone is friendly in a “we might be friends by noon or never speak again” kind of way. You smile, nod, exchange names you immediately forget, and reassure each other that yes, the weather looks good, even though none of you actually control it.
Then the walk begins, and the characters reveal themselves.
There’s Seedorf. Vibrant. Unbothered. A professional hiker in the truest sense. One minute he’s right next to you, laughing and moving with ease, the next minute he’s somehow… gone. Already ahead. Already disappeared into the trail like he merged with the mountain. And just when the group energy dips, he reappears casually, drops “Upepo runda,” and vanishes again. No explanation. Just vibes. You don’t know exactly what it means, but somehow your legs feel lighter after he says it.
A few steps ahead, you hear it, laughter. Loud. Free. Echoing through the hills like the mountains themselves just heard a really good joke. That’s Vlex and Harmfree, you don’t even need to be part of the conversation to feel included. Their laughter does the social work for everyone. It loosens the group, lowers shoulders, reminds you that joy doesn’t need permission. Suddenly you’re smiling for no reason, wondering why laughter feels so rare in normal life and so available out here.
Then there’s Robert, chatty in that warm, grounding way. The kind of person who somehow remembers your name even if the last time you met was a year ago… and not just your name, but that random detail you mentioned in passing. “How did that thing you were worried about turn out?” he asks mid-climb, like it’s the most natural place in the world to check in on someone’s life. You’re hiking, out of breath, and suddenly feeling deeply seen. Conversations with Robert tend to drift, from trails to work, to family, to life; and you don’t even realize you’ve walked half the route while talking.
Somewhere along the way, the awkwardness dissolves. Conversations flow and fade naturally. You talk about work, then forget about it. You overshare a little. Someone admits they almost turned back at the last hill. Someone else confesses they joined because they needed to be around people but didn’t want to talk too much. Everyone understands that sentence deeply. You learn quickly that hiking with strangers teaches you patience. Someone walks slower. Someone faster. No one makes a big deal of it. People wait without announcing it. Someone offers snacks like it’s a sacred ritual. Someone else reminds you to drink water in a way that feels oddly caring.
Silence sneaks in too, not the awkward kind, but the good kind. The kind where no one feels the need to perform. You walk together, breathing hard, listening to gravel crunch and wind move through trees. You’re not “on.” You’re just… here. By the time you reach the top, these people aren’t really strangers anymore. They’re the ones who saw you sweat. Heard you laugh. Waited while you caught your breath. They’ve witnessed a version of you that doesn’t exist in offices or group chats or curated timelines.
And when it’s over, something funny happens. You don’t cling. You don’t force plans. You just exchange smiles, maybe a hug, maybe a “see you on the next one,” knowing full well that you probably will. Because Outdoorer has that effect, it turns strangers into familiar faces without making a big announcement about it. So no, hiking with strangers isn’t awkward the way people warn you it might be. It’s awkward in a human way. In a comforting way. In a way we're all just figuring this out together kind of way.
And honestly, between Upepo runda, laughter bouncing off hills, and conversations that somehow remember you, it’s hard not to come back.
Lily Waithaka | The Storyteller 🧘🏾♀️
Lily Waithaka is a writer and creative voice at Outdoorer, where she curates a reflective series on belonging, community, and the quiet lessons the outdoors continues to teach us. Her work weaves together story and stillness, reminding readers that healing often begins in connection and with nature. Through her reflections, she explores what it means to belong, to the land, to each other, and to ourselves. Each trail and story is a return.