I can hardly ever recall the names of strangers. Over the years, they've blurred into a mosaic of incidental encounters—a cashier wishing me a good day, a fellow passenger offering small talk about the weather. But one day, about five years ago, a stranger taught me something I didn’t know I needed at the time: that the smallest moments can shake loose the biggest truths about yourself.

I was standing in line at a coffee shop on a dreary late-spring afternoon in downtown Boston—pockets of drizzle turning into earnest rain. The shop—as trends dictate—had brick walls, Edison bulbs, and baristas in mandatory flannel uniforms. My mood fit the weather perfectly: unremarkable, slightly damp, and more focused on getting caffeine than engaging in meaningful human interaction. That is, until she arrived.

The Unlikely Teacher

The stranger had an air of knowing ease, the kind that immediately makes you feel two things: underdressed and vaguely insecure. She strolled up and slipped seamlessly into the line behind me, a rare confidence radiating from her like heat off cobblestones in July.

She broke the sacred don’t-look-behind-you rule of public queues and leaned forward to comment on something absurdly specific: my scuffed loafers. “Nice Nantucket energy,” she said with a wry smile. I was caught off guard. Who identifies loafers with Nantucket—and how did she know?

In the seconds it took my brain to reboot, I muttered something unintelligible about maritime style being timeless (which, in hindsight, was the world’s clumsiest flex). Without missing a beat, she added, “I bet you have strong feelings about lighthouses, too.”

If she’d been holding a mirror at that moment, I might’ve seen my soul leave my body in embarrassment. She wasn’t wrong. I do have unsolicited opinions about lighthouses—their function, symbolism, and especially their unreliable portrayal in Hollywood.

Who was she, and how was she in my head?

Three Questions That Changed Everything

The line crawled forward, but she stayed behind me, peppering me with offhanded questions. I wasn’t sure if I was being interrogated for fun or if she was preparing to write the definitive expose on "People Who Look Like They Belong on a Schooner."

  1. “Are you one of those people who’d swim in the ocean in February just to brag about it later?” (Yes, but only once, because I hated it and heavily regretted the post-swim brag session.)

  2. “Let me guess—you think living somewhere romantic, like the Scottish Highlands, is the answer to all life’s problems?” (Definitely yes, but only if I also get rugged knitwear and an endless supply of whisky.)

  3. “What’s harder to navigate: the Atlantic or modern relationships?” (No contest, it’s relationships.)

With that last question, she’d aimed squarely at the soft underbelly of my pride. If you had asked me 90 seconds earlier, I would’ve dismissed it as some unasked-for metaphor. After all, who compares the messy depths of human connection to the Atlantic’s icy, turbulent waves?

Turns out, she did—and it was a comparison that stuck with me long after she’d said it.

The Lesson (And How It Landed)

See, at the time of this encounter, I was grumbling through an overly long stint of self-imposed singledom. I’d walked away from a relationship a year earlier that I swore wasn’t “right” (whatever that means). I buried myself in projects, books, and excuses—all to avoid the vulnerable necessity of trying again. Dating felt like setting sail with patchwork sails and no map—a venture equally doomed and exhausting.

But this stranger, with her lighthouse quips and hyper-specific questions, made me reconsider my approach. She challenged me without judgment. “Most people romanticize lighthouses,” she had said in one final, offhanded moment before her drink order was called, “but the truth is, they’re just there to help ships avoid the rocks. They don’t steer anything. That’s your job.”

Weirdly enough, it made sense. I wasn’t steering anything—I was simply drifting, hoping some cosmic current or external force would take me to a collision-free shoreline. Her analogy made me feel seen, but not shamed. If I wanted connection—a real, meaningful connection—I needed to take the wheel. Not passively hope for good conditions but steer. Even if the waters got messy.

How to Avoid Relationship Drift

Reflecting on what she’d said, I realized drifting not only happens in relationships themselves—it happens in the way we approach them. Her words unpacked like puzzle pieces over months, finally cementing themselves into actionable tips:

  • Know the Rocks on Your Horizon. If you don’t know your own deal-breakers, how can you avoid them? Figure out what you need—whether it’s shared values, emotional availability, or someone who laughs at your (questionable) lighthouse humor.

  • Every Captain Needs a Compass. Compass here means guiding principles. How do you handle conflict? Do you give up at the first sign of bad weather, or fight for smoother seas? You make more progress when you decide in advance how you’ll navigate life’s inevitable challenges.

  • Steering Is a Daily Practice. Steering isn’t flashy or grand—it’s mundane persistence. It’s staying curious about your partner's inner world or tending to your own needs instead of waiting for romance to magically flourish.

  • Don’t Over-Romanticize the Lighthouses. Sure, external markers (fate, timing, friends’ unsolicited advice) might flicker as guides, but they can only do so much. Cultivate the strength to steer your own course.

An Ending That Stuck

The stranger left an impression, but not a name. She was long gone before I absorbed the depth behind her comments—possibly too busy charming her next unsuspecting victim with nautical metaphors and spot-on psychoanalysis.

Today, whenever I catch myself retreating into passivity—whether it’s a friendship, a creative pursuit, or yes, a potential relationship—I remember her words. People, like ships, aren’t meant to coast aimlessly or avoid all risks. Risk is part of the deal. After all, calm seas never made bold sailors, and as someone who grew up surrounded by salt and sea air, I’d be a hypocrite to deny that.

On days when I feel stuck or sluggish, I picture her shaking her head at me knowingly. “Nice Nantucket energy,” I hear her say. Maybe this time, I can manage to steer it in the right direction.