How to Talk to the Stranger Driving You Around Town

We’ve never been more divided. We’re all living in our own echo chambers. Nobody listens to each other anymore.

True as these platitudes may be, our cities are full of chances to have meaningful conversations with strangers—and there’s one modern phenomenon that makes it feel more natural than ever: ridesharing.

A few weeks ago, I was driving for Lyft on the South Side of Chicago. The app paired me with a 59-year-old woman who asked me to call her Entendre. That week, I was asking each of my passengers to tell me about a time they felt a great sense of accomplishment. Entendre’s answer: a brief moment when—as a 9-year-old growing up in Nashville, Tennessee—she discovered she could ride her bike no-handed while braiding her hair at the same time. When I asked her why that’s such an important achievement to her, Entendre told me the experience taught her what it meant to be in the present moment. “I had relaxed into the turn,” she said. “I was one with the bike. It was a big experience because it captured so much of what I love, what’s important, and what has been confirmed as important.”

A few minutes later, I asked her, “Where do you need to be?”

“Nowhere,” Entendre said. “And what is nowhere? ‘Now’ and ‘here.’  Nowhere.”

My ride with Entendre happened almost exactly a year after I quit my job as an anchor/reporter at NBC Chicago to become a Lyft driver. Disillusioned with the state of local news and my role in it, I signed up for Lyft, outfitted my Subaru Forester with microphones, and launched a weekly podcast called Backseat Rider. My goal is to capture authentic stories—an antidote to the “news guy with a microphone” approach that seems to lead through all the expected straits. For each episode, I pick a topic or question to explore, and my passengers become the cast of the show. Occasionally, the questions are news-related; women had countless appalling anecdotes to share after hearing Donald Trump’s “locker room” comments. But mostly they’re universal: what’s the biggest risk you’ve ever taken? What keeps you up at night? What’s your biggest regret?

Almost 50 episodes into the podcast, passengers have allowed me to record some of the most intimate details of their lives, from childhood trauma, family dysfunction, fears, and insecurities to crowning achievements, spiritual views, and the stories of the people they both love and loathe. With the intimacy of sharing a small, private space, these rides often seem like brief, purposeful visits to a stranger’s living room.

When it comes to getting a ride around town, we’re living in a Goldilocks Zone. Taxis, with their plexiglass dividers and often unsociable drivers, are on the decline. Driverless cars, which promise fleets of human-free transit options, are still at least a few years away. That leaves us in a unique window in history where we travel with others in one of the most natural places for conversation: personal cars.

It might have been easier to reach deep conversational territory a few years ago, when ridesharing was still in its infancy. Remember when the novelty of the experience was an icebreaker in and of itself? (I just got into your car, it’s weird not to talk, right?) Until late 2014, Lyft actively encouraged its users to sit up front and fist-bump their drivers. I’ve since driven passengers who still do that. But now that ridesharing is in its adolescence, many riders and drivers have grown weary of small-talk, are unsure if social interaction is expected, and default to riding in silence.

There’s nothing wrong with sharing silence. Even though I always try to initiate conversation, about 10 percent of my Lyft rides are mostly silent. There are some days when it seems like no one’s feeling social. But as long as you’re polite, silence won’t affect your rating as a passenger or as a driver (you know the drivers rate you, too, right?). Thankfully, breaking the small-talk barrier isn’t all that hard if you know what to do.

Even on a short ride, small-talk can easily morph into big-talk if you challenge yourself to aggressively listen. Some of the most common questions you’ll hear at the beginning of a ride—“how’s your day going so far?” or “what made you want to become a driver?”—can be the seeds of a meaningful interaction if you pay close attention to the responses. I once drove a man who’d just dropped off a U-Haul. My simple inquiry into where he was moving led to a triumphant story about his troubled, violent upbringing and how—for the first time in his life—he was going to be living in a safe neighborhood.

Part of aggressive listening means gauging the enthusiasm of the response; it’s an indication of whether that person is interested in talking further. It’s also important to give verbal cues to the other person that you’re listening closely. It amazes me how shocked some passengers are when they realize they have my undivided attention. If a passenger drops the name of their child, for example, I’ll be sure to mention that name in a follow-up question. Knowing they’re being heard makes them want to connect even more.

When the conversation gets real, it’s important to consider the power of quid pro quo. If someone shares something vulnerable with you, consider sharing something vulnerable in return. Don’t expect anyone to open up to you if you’re not willing to do the same. This creates trust and forms a true bond. Even if that bond only lasts a few minutes, it’s still real. Based on the hundreds of rides I’ve given, I believe most people take a degree of comfort in opening up to a complete stranger, knowing we’re unlikely to see each other again.

It may sound obvious, but consider bringing up whatever’s actually on your mind. This is the shortest path to an authentic interaction. One of the most popular episodes of Backseat Rider was born out of what started as a miserable morning. I woke up exhausted and unmotivated, but forced myself to get in the car and drive. Instead of pretending to care about some other topic, I channeled my mood and asked all my riders, “How do you power through your day when you’re feeling exhausted and unmotivated?” The question came from such a genuine place that I got equally genuine responses in return. The conversations made for a great episode, and I still remember all my passengers’ advice.

And finally, there’s one question that’s almost guaranteed to start a genuine conversation: “Could I get your take on something really quickly?” Few people say no to this question. It cuts right through any background noise, empowers the person answering, and stokes curiosity (“I wonder what they want my take on?”) Suddenly, you have carte blanche to bring up pretty much anything you want.

Breaking the small-talk barrier isn’t always easy, but it’s almost always worth it. It makes sitting in traffic more bearable, removes us from our phones, and places us in the present moment. When we rideshare, we’re always going somewhere. But in the meantime—as my passenger Entendre would say—it’s good to be nowhere: now and here.