The Road Not Taken

I’ll never forget the smell of salt in the air that day. It had rained earlier, slicking the cobblestones in Kennebunkport, making me think that if anyone were to fall dramatically during a life-altering moment, this was the stage set for it. I was sitting in my favorite café, chewing thoughtfully on a corner of a blueberry scone, staring down the pages of two very different futures. The first was a steady teaching job back home, complete with colonial charm and family dinners. The second? A one-way ticket to England, where a year of literary indulgence awaited me. Robert Frost said it best, and on that dreary morning, I stood at my own fork in the road.

Some choices sit with you longer because they’re tied to something fundamental: Who am I? And, if we’re to believe the musings of every rom-com protagonist, who do I want beside me for the ride? Spoiler: I chose England—but the road not taken still lingers like the smell of low tide when you're too far from the shore to see why.

The Pull of the "What If"

That overlooked path—whether it’s the one that didn’t get picked or the spark that fizzled too soon—has a way of hanging around like a lighthouse beam in the distance. It feels like potential left untapped, the glittery mystery of everything that could’ve been.

I sometimes imagine what life might’ve looked like had I stayed put. I can practically see my 25-year-old self schlepping around stacks of American lit anthologies, grading papers in the breakroom with a thermal mug of black coffee. Maybe I’d have married someone grounded—sensible enough to wear socks with his boat shoes, charming enough to know better than to call them loafers.

But then I remember: while this version of me would undoubtedly have found joy in her quiet routines, she’d never have spent hours in Shakespeare’s birthplace debating the merits of sonnet structure with British locals over a pint. She’d never have traveled solo along foggy cliffside roads, singing Billie Holiday to herself for courage. She’d never have met Adam, the cheeky Englishman who mistook me for a waitress (to his credit, I was holding another diner’s soup by mistake).

Second-Guessing the Second-Guesses

It’s oddly similar to dating, isn’t it? The ones who got away—or more truthfully, the ones we walked away from—have a way of haunting our better judgment. Maybe we broke up before things got truly serious, or maybe we didn’t swipe right in the first place. They become rose-tinted ghosts, frozen in perfection because we never stuck around to see their socks on the floor or their dish of “creative nachos” that is both unseasoned and unapologetic.

In the spirit of Frost’s dilemma, I’ve come to realize the trick is not letting the road-not-taken syndrome convince you that every missed turn had a pot of gold parked just around the bend. People (and paths) are never as flawless as we imagine when we’ve removed ourselves from their everyday realities. Remember this the next time you’re inclined to cyber-stalk an old flame: they’re no longer six-pack abs and a golden retriever. They’re probably an air fryer enthusiast with a second mortgage.

Mind the “Shoulds”

From your career to love life, the biggest threat to your peace of mind might just be that internal monologue of “shoulds.” Back then, sitting at the café, part of me felt like I should stay. It was the safe choice, the practical one, the decision with fewer moving parts and no time zones to cross for the holidays. One voice in my head—all buttoned up like my high school headmistress—proclaimed, “Don’t be silly now, Charlotte. You’ll regret leaving everyone and everything you know.”

But the louder part of my soul—the part that swoons over Yeats and antique bookstores—wanted adventure. It craved scenes I could later immortalize in writing, tension I could only find by stepping off the well-trod path. If there’s one takeaway here, let it be this: the path worth taking is the one that's truly yours. Whenever “shoulds” creep into your decision-making process, swat them away like a passing mosquito.

What I Learned from the Path I Did Choose

The roads we take shape and shift us. To the surprise of no one, my English adventure wasn’t all romantic clouds of clotted cream and Jane Austen daytrips. There were lonely moments—ones where the Atlantic Ocean felt heavier than ever and all I wanted was a Maine summer sky. But those struggles built a kind of resilience that changed me, the quiet confidence that comes when you figure out how to ask for directions in a foreign town—or a foreign life.

On the dating front, too, I’ve embraced this idea that the choices we make—even the messy ones—lead us toward clarity. My relationship with Adam didn’t last, but it taught me what I value most: partners who bring humor to awkward missteps (and who don’t eat in complete silence—beware the silent eaters).

Mistakes have breadcrumbs of brilliance baked into them, but so too do the victories. And let’s not forget, sometimes things come full circle. That steady teaching role I turned down? It now feels like a parallel universe version of me that I wave at fondly through the looking glass. Instead, I count myself lucky to write for you and help demystify the maze of modern relationships.

Where All Roads Lead

To anyone stuck at their own metaphorical crossroads—whether it’s the choice between two cities, two relationships, or just two options on a takeout menu—here’s my heartfelt advice: trust where the pull is strongest. Not the pull of guilt or convenience, but that tug deep in your gut you can only ignore at your own peril.

The road I didn’t take taught me not to be too precious about any single decision. Whether we trade comfort for uncertainty or vice versa, what matters isn’t the path itself but how we let it mold us. Missed opportunities aren’t failures—they’re just good stories waiting for the right lighting.

If nothing else, remember this: in love and life, there are very few genuinely bad roads. The secret is in owning the one you’re on—and maybe carrying your own blueberry scone for fuel.