Photo: Seth Rader

I’m not entirely sure what I’m doing on a familiarization tour (industry jargon for ‘everything’s paid for in exchange for your coverage’) of North Adams, Massachusetts — an old mill town, 50 miles east of Albany — other than desperately trying not to text a boy who’s somehow become my lifeline.

I cut into my blue-cheese-and-apple burger to reveal a crumbly mess of grayish-brown meat. Letting out a sigh of remorse. I’d ordered medium rare. All of a sudden, I find myself trying not to cry.

The waitress is a flouncy 40-something with big, curly hair and a little too much conversation for my appetite tonight. Yes, I’m here alone. No, I’m not from here. Yes, I would like another drink. End story.

It just started raining and it looks like I’ll be stuck at this small town sports bar in the Berkshires of Western Massachusetts for a while. There was no parking anywhere near the restaurant. I forgot an umbrella.

“How’s that burger, hon?”

“It’s great, thank you!” I sputter with awkward enthusiasm.

A heavy suck on my fake-lime-infused margarita allows me to recover.

Inhale. Exhale. Swallow back cheap, tequila-flavored tears.

* * *

Most people are smart enough to see past the caricature of a travel writer — the cliché crafter, lounging on a beach with a free cocktail in hand. Fellow writers, bloggers, and social media expressionistas have revealed that it’s not all complimentary rooms and free meals. It’s long days hopping from hotel lobbies to galleries to a brewery that looks just like the last five. It’s early mornings and late nights, squeezing out words that may never be read.

But that doesn’t matter to the dreamer — the writer — the one who imagines capturing a destination so perfectly that a reader stops, looks up from the page (or screen) and sees it vividly, their breath stuck in their chest as they experience a moment of pure place.

From the manic energy of New York City to the sharp chill of mountainous Bolivia, my words never seem to properly align with the thrill of seeing, hearing, and feeling these places for myself — but I keep trying.

I smile back and slip a ten-dollar bill under my margarita glass, wondering how long I’ll be able to survive on overtipping. Somehow, even free meals are stretching my budget.

Travel writers strive to summon the spirit of a place in a way that immortalizes their own experiences. But right now, in this rural sports bar with abrasive noise and sickly lighting, the idea of immortalizing this burger seems miserable, even if it is free.

My eyes jump back and forth from the pervasive big screens blaring a baseball game, to the families clustered around messy tables (did that mother look miserable or just happy in a simple sort of way?), to my menu (I should have ordered a beer), and always back to my phone — its screen still desperately dark.

* * *

So the boy.

I met him on a spontaneous vacation to San Francisco. We’d made eye contact over matching ciders at Shotwell’s, his local haunt in the Mission District where groups of tech guys clustered around a pool table. Most of them averted their gaze when my girlfriends and I entered the room, causing an audible shift in the social balance of the establishment — a cliché of the San Francisco dating scene with its gender imbalance, legitimized. But he had looked straight at me and approached with confident conversation and a warm smile.

We spent a whirlwind evening together, hopping in and out of Ubers to all of his favorite bars until we found ourselves kissing beneath the twinkling lights of the Oakland Bay Bridge. He showed me the San Francisco he loves, while I shivered beneath his arm in the chilly summer night.

The next day we said our goodbyes without acknowledging the thousands of miles that would soon come between us. I texted him a photo of the Brooklyn Bridge as my taxi driver brought me home, and suggested he come experience the view in person.

A couple of long distance phone calls later and he was booking a flight to New York City, where we would continue our adventures in understanding two very different cities on opposite sides of the country — he marveling at the abundance of dive bars in Williamsburg, while I continued to poke fun at his lack of Grubhub options in San Francisco.

Showing him around a city I love felt even better than writing about one — the purity of place so effortlessly expressed through my desire to help him understand it.

But despite my love for Brooklyn, I wasn’t going to be there much longer.

“You could just not go on your trip, and come to San Francisco instead…” he’d tentatively offered towards the end of our New York affair.

The trip he was referring to was a drive around the country — a four-month journey I’d been planning for the past year. I was going to live the Great American Road Trip story, only with a feminine slant that had been left out of the genre when Jack Kerouac took the wheel. It was my chance to push my writing to the next level.

We said goodbye again, with mutual promises to keep in touch, and a gaping silence regarding our future.

* * *

I wasn’t going to cancel this trip for a guy. I couldn’t. But I was going to call him, a lot. And now, as I stare at my burger with tears brimming my eyes, my lifeline isn’t answering. Which inevitably leads to the nightly haunting of questions I don’t want answers to.

Was he seeing someone else in San Francisco?

Was he not up to the challenge of dating someone who is professionally and emotionally incapable of staying in one place?

Was I not worth waiting for?

The sight of my black screen taunts me with an endless loop of self doubt.

Families are filling the restaurant now, and the stout, wooden bar that holds up the low ceiling in the middle is surrounded by smiling guests who greet each other with hearty hugs and conversations picked up from the night before. None of them seem to notice that the burgers are terrible.

I pull out a pen and my notebook, but I’ve got nothing to say.

Stories are hard to come by in the isolating loop of eavesdropping and text-message checking.

Succumbing to my burger with small, deliberate chomps, I sense a rising anxiety that none of this is what I set out for.

Where is the adventure in experiencing this trip alone?

Would I ever be offered more than a free meal for my writing?

What the fuck am I doing with my life?!

“You’re all set hon,” offers my waitress with a genuine smile. The meal has been paid for by the tourism board.

I smile back and slip a ten-dollar bill under my margarita glass, wondering how long I’ll be able to survive on overtipping. Somehow, even free meals are stretching my budget. But a shorter trip wouldn’t be so bad.

By the time I open the door to my room at the “stately yet inviting” bed-and-breakfast that has also been provided by the tourism board, I’m soaking wet.

Voices from the porch drift up to my window as I change out of soggy clothes. The owners have family over, and I suddenly remember I’d been invited to join. Their floating conversation feeds me images of them laughing and drinking wine beneath the glow of the porch light. I can smell the citronella from here.

But I’m not going to join them tonight. Instead, I decide to turn my phone off. No texts are lighting up my screen, as much as I stare at it. I take a deep breath and make myself comfortable on the couch next to the window — savoring the company of their presence below — and I write.

It isn’t magic. It isn’t perfect. But in this moment, it’s getting closer.

Sitting there with the heat of my computer radiating through the skin of my lap, my fingers typing furiously, I realize that dreams are always a little lonely. Otherwise, they wouldn’t be yours.

In this moment, I am lucky to be pursuing mine.

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