When you grow up in a place like Bar Harbor, risks tend to look a little different. You’re not wondering whether to cross a bustling intersection in five-inch heels; you’re deciding whether it’s smart to scramble across a patch of wet seaweed knowing there’s a fifty-fifty chance you’ll belly flop onto a barnacle-encrusted rock. Life in Maine teaches you pragmatism—and bruises your shins—but it also tempts you to let the tide pull you toward something new.

For me, the greatest risk I’ve ever taken wasn’t on a slippery shore. It was something scarier than any rugged trail, and yes, it’s completely out of character for someone whose idea of danger is hiking without a granola bar in her pocket. It was the summer I stood on the edge of predictability, held my breath, and told someone how I really felt. Spoiler alert: it was about as graceful as slipping on that wet seaweed, but what I learned changed everything.

The Safety Net of Silence

Before we get to the life-altering confession, let me introduce you to my default setting in relationships: comfortably awkward. I’ve always been more at home noticing hoof prints in the dirt than picking up on romantic clues. Mushrooms? Adorable. Heartfelt stares? Terrifying. In college, my friends joked that I had the attention span of a shorebird when it came to dating. I’d flutter toward connections, only to get skittish if things became too real.

That behavior followed me into adulthood. Like the rocks at low tide, keeping your feelings to yourself feels safe, immovable. As it turns out, though, not saying what’s on your mind doesn’t prevent change—it just allows the waves to erode your chances without resistance.

Fast-forward to three years ago. I was living in Portland for a short writing gig, weathering the kind of winter that makes you question why you willingly live anywhere north of Boston. My saving grace that season was Jamie, a fellow transplant I’d met hiking Bradbury Mountain. We bonded instantly over a shared love of trail maps and an irrational fear of aggressive seagulls. He laughed at my penchant for quoting “Parks and Recreation,” and I listened with rapt attention to his stories about growing up on the Kennebec River. We spent hours debating the secret to Maine winter survival—he swore by wool socks, I pushed hot cider spiked with whiskey—and I didn’t think too hard about how naturally comforting he felt.

Well, until I did.

The Moment of No Return

By the time spring arrived, it hit me like a rogue lobster trap: I was head-over-hiking-boots for Jamie. You’d think as someone who’d spent her entire life observing nature, I’d have a keener sense of self-awareness. But nope. When you’re so used to swallowing feelings out of fear, recognizing them can feel like spotting an osprey where you expected a gull. Thrilling, jarring, and completely unsettling.

Still, I knew I had two choices. Option A? Play it safe. Keep pretending this was just a really intense friendship built on a shared appreciation for fleece jackets. Or, Option B: take the kind of risk that makes a Mainer like me deeply uncomfortable. I could tell him, out loud, how I felt.

I rehearsed the big moment with the precision of someone preparing for an orienteering competition. Alone in my apartment, I practiced phrases like: “I really like spending time with you,” and, “You make winter in Portland bearable.” What sounded poetic in my head came out garbled in real time, which planted the seed that this whole idea was ridiculous. But something inside me—maybe the tiny portion of my soul braver than a puffin balancing on a gusty cliff—refused to let me backpedal.

So, one drizzly Monday, after a walk along East End Beach, I steered Jamie toward a bench overlooking Casco Bay. The words came out in a rush before I could second-guess them, something like: “You’re great, and I like you, like, in a more-than-friends way, and I don’t know what you’ll say, but I just had to tell you because I can’t not say it anymore.” Riveting stuff, right? Not quite the sweeping romantic monologue of a Netflix movie, honestly more like the verbal equivalent of tripping over a tree root.

The Fallout and the Silver Lining

Here’s the part where you’ll want to know how Jamie responded. Was it a shared revelation? A tearful hug? Fireworks over the bay? If only. He was kind but stunned. He admitted he hadn’t seen this coming and wasn’t sure if he felt the same way. It was... not the outcome I’d secretly hoped for.

But here’s the thing: what came next completely surprised me. Instead of the earth opening up to swallow me whole, there was a strange and unexpected calm. For the first time, I’d faced my fear of rejection head-on, and I was still standing. My admission didn’t unravel the fabric of our friendship as I’d feared—it reframed it. I realized I’d built Jamie up as this mythical figure rather than taking stock of his very real humanity.

After a couple of weeks of awkwardness and space, our friendship recalibrated. Slowly, naturally. And while he didn’t turn out to be my forever person, making my feelings known was my wake-up call to stop hiding behind politeness.

So, Was It Worth It? Absolutely. And Here’s Why.

Sometimes, the greatest risks aren’t about the outcome—they’re about teaching you who you are, what you want, and what you’ll no longer shy away from. Being honest about how I felt broke the pattern of tiptoeing around relationships my entire life. It gave me the courage to face messiness and ambiguity instead of assuming I couldn’t handle either.

Since Jamie, I’ve carried this lesson with me like my favorite flannel shirt—it’s well-worn, comforting, but tough enough to withstand whatever comes my way. And while putting your heart out there might leave you feeling as exposed as Maine’s rocky shoreline at low tide, it’s also the only way to see what possibilities might be hiding just below the surface.

Taking Your Leap: Risking Big for Connection

If you’re feeling stuck in your own version of emotional safety nets, let me offer you a few insights from my stumble-I-mean-success:

  • Stop Overthinking. Just like you can’t predict how a spring hike will pan out (muddy boots, guaranteed), you can’t script someone’s response. Act anyway.
  • Reframe Rejection. It’s not a failure—it’s evidence that you’re brave enough to want something real.
  • Keep Perspective. If telling someone how you feel leads to awkwardness, remember: you’ve survived worse. The first ice slip of winter comes to mind.
  • Reward Yourself. Whether it’s indulging in cherry pie from a local diner or giving yourself a pep talk by the ocean, celebrate the fact you dared to risk connection.

What’s Waiting for You in the Deep End

Confessing feelings might feel as risky as navigating slick rocks at low tide, but trust me, it’s the most exhilarating leap you can take. Will every risk work out as planned? Nope. But every single one teaches you how to show up more fully, more honestly, and with more confidence that, even if you falter, you’re still moving forward.

So, grab your metaphorical hiking boots—or muck boots, if it’s one of those messy days—and push past the fear. Risks like these remind us that life’s richest moments aren’t found on the trail others have cleared for us. They’re waiting in the bramble, where you might stumble, but you might also bloom.