Confessions and Connections—Passenger Shares Dark Secrets

“We become listeners, confidants, and sometimes even therapists for our passengers.”

As a rideshare driver, we often find ourselves playing the role of a therapist. Passengers hop into our cars and unload a whirlwind of life stories, problems, and secrets. They feel safe doing this because of the anonymity of the ride and the understanding that they’ll likely never cross paths with us again. This unique dynamic encourages them to share the most personal and outrageous details—sometimes even more than they would with their priest during confession.

One trip that stands out in my memory is when I picked up a pilot from the small Wilmington airport one afternoon. He had no luggage with him, and honestly, he didn’t look like a typical pilot. He was also headed to the Northeast Philly Airport, which made me curious about why someone would travel between two airports without any bags.

“Oh, I’m a pilot. I just delivered a plane here for maintenance,” he explained, satisfying my curiosity.

He turned out to be quite a relatable guy, radiating family man vibes. We connected well during our conversation. The ride lasted a bit over an hour, and with rush hour traffic slowing us down, so we had plenty of time to get to know one another.

We were roughly the same age and had both grown up in the same Greater Philadelphia area. Both of us were married and had children. At the time, I had one child, while he had two little girls that he said “he loved with all of his heart.” I could sense his sincerity from the way he spoke about them.

Soon he began to share his feelings about his wife, revealing his frustrations about their frequent arguments and that he was unhappy in the relationship. He confessed that if it weren't for his two beautiful daughters, he probably would have divorced “that ungrateful bitch” and moved on—embracing the single life and enjoying the freedom to do whatever “the fuck I want.”

However, the discussion took even more of a dramatic turn when he expressed that he felt as though his life was over. He shared his disappointment with how things had turned out for him. “I don’t earn enough money, at least not enough to keep up with what my wife likes to spend,” he said.

He confessed that he has trouble sleeping and likely suffers from depression. Yet, he’s reluctant to seek therapy because he needs to keep it a secret from the airlines to maintain his pilot license. Instead, he mentioned that he turns to drinking to “numb the pain.”

“I’ll need to deal with it eventually,” he confessed, recognizing that he can't keep living this self-destructive lifestyle without eventually facing repercussions.

At the very least, he recognizes that he has an issue, which is a positive first step. “But I just can’t quit drinking yet because I don’t know how to address my problems,” he continued. From the outside you would never guess that this successful man was hiding such dark secrets that were slowly destroying him.

I was at a loss for words and unsure how to respond, so I chose to remain silent and listen. When he asked if I had ever gone through any challenges in my life, I shared my financial issues following the Great Financial Crisis and the experience of my divorce.

I truly felt bad for him and wished that he would get help he desperately needed, as he struck me as a genuinely decent person who was fighting his own inner struggles. I couldn’t ignore the reality that he operates commercial aircraft, but thankfully, he does it without any passengers on board—he’s only a maintenance pilot.

In the last eight years, I’ve made roughly 10,000 trips, yet I can hardly remember 99% of them. However, there are certain rides that linger in my mind, and this one is definitely among them—especially those moments when passengers unload their emotional burdens on me as if I were their therapist.

However, I didn't sign up to be a therapist that day—that's my wife's job—she’s an actual licensed psychologist. Still, rideshare drivers do play a similar role by listening to people's problems while they’re in our cars. Sometimes, though, I just want to hop in my car, drive passengers around, and not be their confidant.