TRAVEL

I started dating a trucker, then I left Oakland and traveled America with him for 9 months

March 29th, 2021

In August 2019, a week shy of my 39th birthday, I climbed into the cab of a semi-truck in San Diego with a man I’d met just two months before. We were bound for Austin, Texas, and technically, this was our fourth date.

Now, I’m as big of a fan of “not getting murdered” as the next girl, and I’ll be the first to admit that the premise of going on a blind date with a long haul trucker I met online absolutely sounded like an episode of "Unsolved Mysteries" waiting to happen. But as I watched Brandt from behind the bushes outside of the Oakland restaurant Mua, where we were to meet for the first time, I caught no murder vibes. I couldn’t tell you what we talked about during that first date; my heart was beating too hard and the music was too loud. All I knew was that he was handsome, polite and surprisingly wholesome-seeming for a man who claimed to love Lou Reed as much as he does.

In the year that followed, I saw more of the United States than I had in my entire life up to that point. My time spent living and working on the road with Brandt and his (now our) pug Sally, is among the happiest of my life. And it almost never happened.

Instead of playing it cool, as the misguided 1990s romantic comedies of our youth advised, Brandt and I dove in — texting and talking on the phone nonstop during those first two months of long-distance dating. Two weeks into one of his trips, I was in the middle of typing “I wish I was there with you too” for what felt like the millionth time, when I realized that, if I really hustled, in six to eight hours I could be there.

I hesitated only momentarily wondering if driving from Oakland to San Diego at 5 p.m. on a Saturday night to be with some dude I’d only met in person once was the right move. Lyrics from a Bright Eyes song I hadn’t heard in at least a decade came to mind as I schlepped my weekend bag to my car:

Remember the time I drove all night? / Just to meet you in the morning? ... / And now I don’t care, I could go anywhere with you / And I’d probably be happy.

As I set my map for San Diego, I got a text — a link, from Brandt, to that same Bright Eyes song. It had to be a sign, right?

When I arrived, well after midnight, Brandt greeted me in the street. Before I could get out of the car, Sally leapt through my window and into my lap, planting gross but cute dog kisses on my face.

I had wanted to road trip across the U.S. from the time I was a teenager, but the demands of adulthood — work, bills, student debt — had always taken priority. So much of the “traveling” I had done up until this point had been through reliving others’ experiences of a place anecdotally.

Take Austin, for example, where we were headed now: I had wanted to visit since I was in my early twenties, but had never been.

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Suddenly, the fact that my writing work was freelance no longer felt like a personal failing on my part, but kismet. If I had gotten, say, the in-house job I so desperately thought I wanted just a few months before, I couldn’t have been here, about to hit the road with Brandt for the first time.

There is something deeply meditative, almost mesmerizing, about seeing the world from 6 feet above the road through the wide-screen windshield of a semi-truck. During the first several hundred miles of our trip to Texas, I delighted in every cactus, Joshua tree and desert rock formation I saw. I remember the first time we crossed time zones: from Pacific to Mountain in Arizona, and from Mountain to Central as we rolled into Texas.

We stopped and slept for the evening in a sandy truck stop parking lot just south of El Paso, where billboards had sprung up between the super churches and pawn shops, Guitar Centers and gentlemen’s clubs: “El Paso Strong,” “Prayers For El Paso” and a simple one that read: “Enough’s Enough: Ban Assault Rifles.”

Brandt pointed to the helado-colored shanties in hues of fresa, chicle, mango on the hillside across the Rio Grande in Ciudad Juarez. We noticed the way the chones and chaquetas were strung up on clotheslines like family flags. It had been two weeks since a white gunman had killed 23 mostly Latinx people in this border town. This, too, was what seeing America was about.

The next morning, in Austin, we lined up outside of Terry Black’s Barbecue with dozens of strangers. I delighted in the easy way our linemates chatted with us, as though we were all waiting to go on a roller coaster, not a meat bender. This chattiness is a quirk of Southern manners I’ve been charmed by again and again in our travels. Conversation there seems to flow as naturally and without worry as sweat does in the Southern heat.

Though Brandt had a delivery in east Texas the following Monday, and I had a deadline approaching, the weekend was ours. We spent it eating breakfast tacos, sipping iced tea, swimming at Barton Springs, and made a favorite discovery in Cheer-Up Charlie’s, where on that particular night, dozens of Austin’s gorgeous LGBTQ youth were gathered as glam-synth country act Pelvis Wrestley cast musical spells over the crowd.

Over time, our long days on the road began to take on a shape of their own. In the morning, after taking Sally for a walk and scaring up a simple breakfast and some much-needed caffeine for ourselves, I’d work for as long as my Wi-Fi reception and concentration would allow. By the late afternoon, I’d take out my earbuds and rejoin the road trip, aware, once again, that I was in the passenger seat of a white International semi-truck, that from nose to trailer tail measured a cumbersome 70 feet long, rolling cross-country with the man and dog I’d grown to love to the point of inseparability.

On our first date, he’d beamed as he told me about his three sons, all nearly grown, and how he’d gotten his commercial driver’s license at 22, as a means to support them. He and his ex-wife had been separated for over a decade, and Brandt had spent the past five years on the road working for a moving company, reuniting newly relocated people with their worldly possessions.

Once I joined him, Brandt and I passed the time listening to history podcasts, books on tape and an ever-growing playlist of shared songs that was now three months deep. On the days that Brandt had deliveries, I’d have him drop me at a local coffee shop where I could enjoy previously simple pleasures, like free internet and peeing indoors. At the end of those days, I’d come home to the 2018 International LT — or “Kevin” as we’d come to call the truck — having barely gotten my land legs back, my hair and clothes stinking of burnt coffee.

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My time on the road with Brandt lasted nearly nine months. I’d typically join him on the road for a few weeks each time, breaking every so often to tend to medical appointments and my apartment.

We were sharing a gray upholstered living space that was approximately 7 feet by 5 feet. Each and every item we brought with us had to have a designated place. The bottom bunk was not just where we slept but where we played board games, streamed movies and my office on the days I couldn’t get to a coffee shop.

Our first purchase together was a fancy XL twin mattress to ease the back aches that come from two adults — including one who is 6 feet 2 inches tall — spooning in cramped, creative configurations most nights. If one of us had to get out of bed, not smooshing the other person (or the dog) involved a complex choreography. And, almost inevitably, as soon as I was settled in for the evening, Brandt and Sally lulling me with their tandem snoring, I would have to pee.

I would lay there at 3 a.m., unable to sleep, calculating the distance from the truck to the truck stop bathroom alongside the likelihood of getting kidnapped from a truck stop parking lot at that time of night. More often than not, I wound up relieving myself in an extra large plastic beverage cup we’d picked up at a convenience store for this express purpose.

With showers going for $20 a pop, our shower schedule was set to every other day, as most of the truck stops we frequented offered a free shower with every big-rig diesel tank fill-up. About once a week, Brandt’s company would put us up in a hotel for a night or two, where we’d luxuriate in food delivery apps and indoor plumbing.

Over time, I took to cooking dinner utilizing an air fryer, an electric skillet, a rice cooker, a folding table and an extension cord we ran from the cab of the truck outdoors. Meal planning, prep and clean-up added an extra 2 to 3 hours each day to our already tight schedule, but it was better than living on fast food.

From Texas, we cut up through Oklahoma and Kansas, where summer lightning storms lit up the road in silver flashes and mosquitoes savaged my ankles. We stopped in Colorado Springs for a few days, then pushed through Utah and Idaho, where I ogled the giant red and gold rock cliffs that reminded me of old "Road Runner" cartoons. This leg of the trip was two weeks.

Once, in Washington state, following my whimsy one weekend, we wound up at a sheepdog trial on someone’s private ranch. Later, we were 8 miles past North Bend — a town made famous by David Lynch’s "Twin Peaks" — when I realized where we had just been. “Oh well,” I thought, “next time.”

Then I thought of my father, and how one afternoon as I was driving him home from radiation treatments, he’d wanted to take a detour to show me his favorite tree. Over the years, its trunk had nearly swallowed the “No Trespassing” sign nailed to it. But we’d been so busy talking, I missed the turn and said, “Oh well, next time.”

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“There isn’t going to be a next time,” he said. I turned around — and he died five weeks later while I was on a long-planned trip to New Orleans, which he’d forbidden me from canceling.

Since I first watched Lynch’s bizarro noir soap opera with my dad, I’d wanted us to visit South Bend’s R and R Diner together for a “damned good cup of coffee” and a slice of cherry pie. But we never made it, and it had taken me 39 years to get this close. So I asked Brandt to turn Kevin around. The stop meant we would have to make up for lost time later, but it was worth it for our conversations with locals and a long walk in the autumn woods with Sally.

At the beginning of the COVID-19 outbreak, I’d taken a break from my nine months on the road with Brandt and was in my hometown in rural northern California, visiting family. Brandt was on a cross-country work trip with his eldest son, Zion, 21. Suddenly, things like hand sanitizer, anti-bacterial wipes, rubber gloves and masks were impossible to find, and his company didn’t provide him with PPE. To get to running water, Brandt and Zion had to go where other people congregated: truck stop bathrooms, showers at the gym.

To do his essential job, Brandt was required to go into the homes of strangers. For a while, even the fast-food restaurants were shut down, and Brandt sent me photos of empty supermarket shelves. He and Zion got sick out on the road, with chest colds that would not go away and left them weak, but in those early days testing sites were nearly impossible to find. I spent those weeks we were apart in a blind panic, worried for Brandt and Zion, watching as my freelance work dried up, and as the businesses of many of my friends folded overnight.

When Brandt finally got off the road six weeks later, in late April, I made the typically 13-hour drive from Mendocino to San Diego in nine hours flat — the once congested freeways were ghostly quiet.

Now, a year later, our lives look nothing like our early days together on the road. Brandt was laid off, and we decided to ride out the pandemic in the small coastal California town of Fort Bragg, where I grew up. A local trucking company hired him for work that kept him closer to home, delivering items like dialysis machines to our local hospital, dog food to the local feed stores, organic flour to the small bakeries.

Our two-bedroom apartment and queen-sized bed feel palatial compared to Kevin’s sleeper cab, and I am still amazed at how quickly dinner can be made with access to four burners and a sink.

On occasion, Brandt still goes on longer out-of-town trips, running fish from our local harbor to markets in Fisherman’s Wharf or organic soil from Humboldt to LA. Whenever possible, I go with him. But for now, without it feeling safe to go to restaurants or see live music, the road has gone from a place of spontaneity and possibility to one where we, by necessity, continue our isolation.

Like many of us, most of the traveling I did in the past year was in my memory and imagination. Knowing now, as my father had, that there isn’t always a “next time,” I often think of how lucky Brandt and I were to find each other before the world shut down, and that together we got to take in this country as it was, before riding, alongside everyone else, into what it may yet become, post-pandemic.

Curated By

Maya Gupta
Investigative Journalist | Grassroots Movement Organizer | Economy Consultant/Speaker
Maya Gupta writes from the fault lines of a world that refuses to stay quiet. Focused on the collisions between culture, power, and accountability, her work cuts past polished narratives to expose what’s really moving beneath the surface. From the rise of creator-driven influence to athlete activism and grassroots resistance, she tracks the momentum shaping a generation unwilling to wait its turn. Her reporting doesn’t cater to comfort, it confronts it, challenging institutions that lean on legacy instead of legitimacy. With a voice rooted in urgency and a lens tuned to those often ignored, Maya delivers coverage that reflects the stakes as they are, not as they’re packaged. This is journalism that doesn’t just observe change, it stands in the middle of it, documenting the push, the backlash, and the undeniable shift underway.

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