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.
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 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.”
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
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.”
“You don't want to overwhelm them,” Aron says. “You have to start with less central things.”
“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.”
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.”
A deeper conversation isn't built on great questions alone. It hinges on whether the other person feels heard.
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
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 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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