Most people slide into Robert Roble’s car, pop in their earbuds, and signal that they’d rather not talk. Roble has spent eight years and nearly 12,000 Lyft rides trying to change their minds. By the time he pulls up to their destination, a surprising number have taken their earbuds out, and some have told him it was the best conversation they’d had in weeks. While many of us assume strangers want to be left alone, Roble is cheerful proof that we’re often wrong—and that the distance between small talk and real talk is shorter than it looks.
His method isn’t charm so much as attention. Before he pulls away from the curb, the 60-year-old Atlanta-based driver has already clocked the small stuff—a team jersey, a work badge, the slump of a long day—and fine-tuned his approach to the person. Younger riders, he’s found, light up about a player like LeBron James but go cold on the local team, while older ones would rather talk teams than names. His opener, though, is disarmingly simple: He asks how to pronounce a passenger’s name.
“I’ll throw something out there, see if it sticks, and usually it comes back,” he says. As for the earbuds? “They’ll either keep them on and talk to me, or pull one off, or take the whole thing off.”
What Roble figured out by trial and error, researchers have measured. People badly underestimate how interested others are in connecting—and how good a deeper conversation will actually feel, says University of Chicago behavioral scientist Nicholas Epley, author of A Little More Social: How Small Choices Create Unexpected Happiness, Health, and Connection. His research suggests that we brace for awkwardness and come away happier, more connected, and more understood than we predicted.
The skills that get you there can be learned. Here’s how to turn a surface-level conversation into a more meaningful one.
Be the one who goes first
The hardest part of any deeper conversation is the moment before it starts, and someone has to be willing to make the first move. “Meaningful conversations usually require a small leap of faith—a small moment of courage,” says Alison Wood Brooks, a professor at Harvard Business School and the author of Talk: The Science of Conversation and the Art of Being Ourselves. “Someone has to go first.”
You can make that leap easier by sharing a little about yourself first. “Self-disclosure is contagious,” Brooks says. “When one person shares something slightly more personal, funny, or vulnerable, the other person often feels permission to do the same.”
Epley recalls a skeptical colleague who decided to put the idea to the test on a train from San Francisco to Los Angeles. A woman sat down beside him with a little Pomeranian in a carrier, and he started by complimenting the dog. By the end of the trip, she’d told him how she’d grown up in a strict religious household, nearly been married off as a teenager, and broken away from both her family and her church—and the two of them, near tears, were hugging. “That was the first time he tried to actually do this,” Epley says.
Start small, then go deeper
Resist the urge to dive straight into the deep end—it tends to backfire. “It’s a little scary to ask about too much, too quick,” says Arthur Aron, a psychologist at Stony Brook University who created the famous “36 Questions“ study designed to help strangers feel close.
Instead, think of connection as something that builds in stages. “You talk a little bit—not too deep—then a little deeper, and move gradually to deeper things,” Aron says. “That usually works best.”
Aron’s questions follow the same logic. They begin with light prompts—“What would constitute a perfect day for you?”—and slowly move into more personal territory. The heaviest questions come at the very end: how you’d feel if your mother died, for example, or what you’d most want to tell a loved one if you knew you were going to die tomorrow. Those questions can be powerful once trust has been established, but as an opener? Don’t be surprised if the other person starts scouting escape routes.
“You don’t want to overwhelm them,” Aron says. “You have to start with less central things.”
Go beyond the facts
You don’t have to ditch small-talk staples, like asking someone what they do. You just have to use them as a launchpad. “Shifting from questions about what to questions about why is a good way” to get somewhere real, Epley says. Often, it’s just a matter of tweaking the question you’d ask anyway. “What do you do?” becomes “What’s the most rewarding part of your work?” “Where did you grow up?” becomes “What was it like growing up there?” Same territory, but now you’re asking about the person, not just the facts of their life.
“Your second question can go from something on the surface to something about the person—their beliefs, their feelings, what they love, why they’re doing something,” he says. The whole thing gets easier if you walk in genuinely curious: “If you take an interest in somebody, the questions will come to you.”
Once you’ve established a little rapport, it helps to have one reliable question ready to reach for. Aron keeps a few tested ones in his back pocket for exactly that moment: “What’s really meaningful in your life right now?” “What are you looking forward to?” And: “What are you struggling with?” “They think about it for a minute, and then they say something,“ he says—and the conversation tends to take off from there.
Keep asking the next question
Most of us pour our energy into a clever opening question and then scramble to change the subject. Yet “the magic often happens in the second, third, and fourth questions,“ Brooks says. “Following someone’s curiosity rather than jumping to a new topic signals that you’re genuinely interested in them.”
The next question is usually hiding in the answer. “If someone mentions a recent trip, ask what surprised them most,” Brooks says. “If they mention work, ask what they’re excited about right now. If they mention their family, ask what they’ve been learning from their kids lately.” Her rule of thumb when you’re not sure where to go: “When in doubt, ask the next question.”
Show them you’re really listening
A deeper conversation isn’t built on great questions alone. It hinges on whether the other person feels heard.
According to Aron, that comes down to three things: showing that you understand what they’re saying, acknowledging why they might feel that way, and letting them know you care. He sums it up in three words: “understanding, validating, and caring.”
That doesn’t require a perfectly crafted response. Sometimes it’s as simple as saying, “I can see why that upset you,” or “That sounds like a big deal.” The goal isn’t to solve the person’s problem, he says; it’s to show that you’re with them.
Don’t make it an interview
There’s a catch to all those follow-up questions: Fire off too many, and you’ve built an interrogation, not a connection. “A good conversation is not purely a data-collection exercise (too many questions) nor a monologue (too few),” Brooks says. “It’s a collaborative process of discovery.” The fix is to keep trading; share something of your own before asking the next question, so the conversation is reciprocal.
Practice—it gets easier
If all of this still feels daunting, the only real cure is reps. “The way to change perspective here is to gain lots of experience,” Epley says. “That’s the only way we know how to do it—go out and practice it.”
The payoff is bigger than a good chat. “It’s empowering,” he says. “Too often we hold ourselves back from reaching out and engaging with other people because we’re overly pessimistic about the consequences.”
The more often you do it, the more you realize that most people are more open to going deeper than they seem. Many of us, Brooks says, are simply waiting for permission to be a little more human with each other. And that’s the point. The best conversations aren’t interrogations or confessions. They’re “two people discovering what’s interesting, meaningful, and human about each other—and having fun along the way.”
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