How an Amtrak Train Trip Sparked a Romance, and Changed the Way I Date

One day while I was home sick, languishing in bed and binge-watching reality TV, I stumbled upon The Millionaire Matchmaker. The matchmaker, Patti Stanger, asked a cadre of beautiful women, “Where are you going to meet the people you want to meet? If you want to meet a doctor, you’ve got to hang out at restaurants by the hospital. If you want to meet a lawyer, frequent bars by the courthouse after work. You must go where the people you want to meet are, increasing the likelihood of crossing their path."

This piece of advice stuck with me. I had been single for the better part of a decade. It wasn’t that I was looking to meet and marry a millionaire, but I was interested in meeting a man whose life experiences dovetailed with mine. A man who was financially independent and successful. I was entrepreneurial. A writer. A business owner. And I was a full-time single parent of a 10-year-old boy. These experiences shaped my worldview so much that I often found it challenging to connect with men who I didn't have more than one in common with. But unlike doctors and lawyers, identifying a place to meet an entrepreneur or writer with kids seemed a little trickier.

Since my divorce, most of the men I'd dated, I’d met online. But I found dating online to be an uneven experience. While I’d met some good guys, I’d also encountered men who had misrepresented themselves: on a sabbatical as opposed to unemployed, on a road trip as opposed to living out of a car, single as opposed to married. I was working hard to provide for myself and my son, and I was interested in finding a partner who could do the same.

I’d often thought traveling would be an excellent opportunity to employ the matchmaker's advice. For instance, flying first class might provide a perfect opportunity to meet a worldly man who was also self-sufficient. But traveling lay outside my budget, much less first class.

However, with a few days to myself last February, my college roommate invited me to join her at her family's condo on Coronado Island just off San Diego. She suggested I take the train down from my home in Los Angeles. While flying first class was out of the question, I thought first class on a train might suit my budget. And indeed, it did.

I met Mark on Amtrak’s Pacific Surfliner en route to San Diego. We sat across the aisle from each other, the gleaming Pacific Ocean whizzing past us on our left. We struck up a conversation when we both ordered Chardonnay at noon. Thanks to our business-class tickets, Amtrak's equivalent of first class, wine was free. Snacks, too. Mark said he was an investor in the restaurant industry, and bound for Tijuana to check out the food scene. Perhaps I was apprehensive given my difficult dating experiences, but I'd adopted a healthy dose of skepticism regarding any potential suitor.

He looked clean-cut, buoyant, and business-y. Outfitted in sportswear, donning earbuds, and with a close crop fade hairstyle, he looked like he’d just sprinted for the train while on a conference call. Banter came easy to us. Air felt lighter around him. I enjoyed his company. And thanks to the masks Amtrak required we wear at the time, for much of the ride, I could only see half his face — though the half I saw, I liked.

When Mark pressed pause on our conversation so I might “get back to work,” he said, referencing the papers strewn out before me, there was plenty on the train to distract me. Prominent outlets to power my laptop, Wi-fi (though it tended to be spotty), and a majestic ocean competing for attention on my left. I enjoyed the gentle rocking motion of the train. In fact, I found it so soothing, it lulled me to sleep. The wine may have helped. (Mark told me later I’d fallen asleep snoring with my mouth open.)

When I woke from my nap, I was surprised (and disappointed) to find Mark no longer seated across the aisle from me. Two girls were sitting there in his place. My disappointment was short-lived when I learned Mark was now seated behind me. He confessed he had relinquished his seat so two friends could sit together. Most travelers on the train had commandeered one of the two seats on either side of the train. I found it interesting that Mark chose to sit behind me instead of next to me. I had an open seat on my right. Was he afraid I'd get the wrong idea?

Despite how much I enjoyed his company, I wasn't sure if Mark was interested in me. Or, if so, in what way. When the possibility of meeting up in San Diego arose, it quickly dwindled after Mark revealed he wouldn’t be back from Tijuana till Saturday. I was scheduled to leave San Diego on Friday. Though upon this discovery, Mark suggested we meet for a drink back home in L.A. I bounced my brows and replied in no uncertain terms, "I'd like that." I stopped short of clapping and jumping up and down. In the meantime, Mark offered to text me some restaurant recommendations my friend and I might enjoy during our stay in Coronado.

While meeting Mark that day seemed fortuitous, I now realize several calculated steps I took on the train in hopes of meeting a man with whom I had more than one thing in common — everything from where I sat to what I ordered to how I chose to carry my luggage.

For instance, I purchased Amtrak’s one-way business-class ticket on the Pacific Surfliner, instead of a fare in coach. The Pacific Surfliner runs along the southern coast of California between San Luis Obispo and San Diego. I told the conductor it was my first time traveling on the Surfliner and asked him where he suggested I sit. He said, if I wanted a good view of the Pacific Ocean, sit on the left-hand side of the train. He also added that the second top-floor cabin (top-floor cabins are reserved for business class) was nicer and more comfortably upholstered than the first. Fate also played a role on the train that day. Unbeknownst to me, Mark had already selected the seat across the aisle from mine when I sat down. He was in the forward cabin when I arrived.

I didn't initially order wine on the train that day, concerned about what my fellow travelers might think. Wine on a weekday at noon? But I was on a trip on a weekday, by myself, without my boy. This was no ordinary day for me. I was on vacation. Still, I refrained. But when I saw Mark order wine from across the aisle at no cost, I asked the conductor if I could trade my unopened Diet Coke for a miniature bottle of Chardonnay and a plastic cup. He obliged. This exchange sparked a conversation between Mark and me, where I confessed I had succumbed to wine envy. He asked what I was working on; I told him I was a writer.

Because I’m a single parent, I’m independent. Before my trip that day, I had reminded myself that if someone offered to help me during my travels, I should thank them and not deter them, as is my tendency. After all, this provided another opportunity for connection, and chivalry was a quality I valued in a potential partner. Now, I didn’t stuff an anvil in my bag and act helpless, but when Mark offered to carry my suitcase down the stairs and off the train, I smiled and thanked him.

Another advantage of meeting someone while traveling is that, provided you are hitting it off, you are a captive audience to each other for the time you’re in transit. Meeting while traveling also allows for greater intimacy. You’re on neutral turf and can let your guard down because, hey, you may never see each other again. Meeting on the train gave Mark and me a low-pressure opportunity to get to know one another in person. And I didn’t have to pay for a sitter. Or an Uber. Or a first date that can sometimes feel forced, awkward, and disappointing.

At one point during our time on the train, I probed Mark further on the nature of his investment business in the restaurant industry.

“Restaurants,” he replied.

“You own restaurants?” I asked.

“Yes, well, one’s a food truck.”

Discussing his business seemed to make him uncomfortable, or so his body language told me. So, I abandoned the topic, with plans to revisit it later.

Toward the end of our train ride, Mark asked for my number. I gave it to him, including my first and last name. He texted me his as we pulled into our final stop. He carried my bag off the train, we wished each other farewell with plans to reconnect, and then parted ways in the downtown San Diego Santa Fe train depot.

When I thought to myself that day that Mark owned a food truck, it wasn’t till weeks later that I learned he not only owned a food truck, but he had revolutionized the food truck industry. (I learned this when I Googled him before our third date, at which point I told him so.) Along with his friend and business partner, who is now a celebrity chef, Mark spawned an entrepreneurial food truck movement worldwide, even inspiring a hit Hollywood movie. Given my dating experiences with men who had inflated their accomplishments, or even flat-out lied, Mark choosing to downplay his success only endeared him to me more. He was a chef by trade and an entrepreneur with a 12-year-old daughter. He had also been divorced for about a decade. Working my dating strategy into my travel plans had worked.

Though while I had successfully used travel as a method of dating, the very things that drew me to Mark, the things we had in common, turned out to be what made it difficult for us to be together. Entrepreneurs, by nature, are driven, often prioritizing work above all else. And single parents, by definition, are busy. So, while we had great times together, which included more travel, these things we had in common, the ones I thought were pivotal to our connection, soon made our relationship unsustainable.

Mark was the first man I had met IRL and dated in years. He was the man I had hoped to meet on the train that day. My excitement grew the more Mark and I learned all we had in common. I enjoyed his humor. The wine. It was romantic. And for all my careful planning, inspired by The Millionaire Matchmaker, the main thing I did differently on the train that day was remain present. It was no ordinary day for me, that’s true. Time stopped on the train. And, like good travel forces us to do, I steeped in my surroundings. The glittering Pacific Ocean, the rhythmic swaying of the train car, the conductor calling out stations. And the stranger on my right. I carry this lesson with me in my quest to meet someone new.