How to Have a Great Conversation With Anyone, Anywhere

When I let small talk with strangers spiral into something deeper, it became a book about memorable interactions. Here’s what I learned.

Photo: Getty Images / janiecbros

The best conversations crack us open. They leave us tender and reeling, alive again with possibility, mesmerized by the uncanny nature of things. When you really “get there” with someone, you reach what my friend once referred to as the wilderness. You may not know where you are anymore, but you know it’s a place of mystery and beauty. You know you want to keep going. I felt this most acutely a few years ago when I kept having unexpected interactions with strangers. I wrote a book about those experiences — No One You Know, which is very much a chronicle of surprising conversations. There may not ever be an exact map, but thinking back on them now offers a few clues at how to reach that wilderness.

Subdue your chauffeur

Conversation is such a fundamental part of everyday life that we all rely on highly skilled autopilots, or “chauffeurs,” as Christopher Isherwood called them, to tow us through situations. That’s the part of you that kicks in to engage without having to think or really pay attention. The chauffeur can offer up your most well-worn stories and get a laugh by telling a favorite joke but when they’re driving, you’re not really present. While an element of repetition and disengagement is necessary for us to get through some conversations (and maybe even an essential part of being a person), it can be problematic when you’re seeking something deeper or different. Step one is to start noticing that you do in fact have a chauffeur. How often do you let them drive? Is it happening more and more? Perhaps it’s time to confront your chauffeur and hurl them out of the car. Take the wheel.

Go off-script

When you talk about the things you always talk about, you’re going to end up with a conversation you’ve had before. The same old terrain. Instead, seek the side roads. Give voice to a random thought or theory you’ve been turning over recently (ex: “I’ve been noticing that I produce different types of writing when I write longhand as opposed to typing”). Bring up something noteworthy that you read, or something strange you saw in the street. A memory that has been returning to you lately. Introduce something that fascinates you. It’s unfortunate that most conversations get confined to the narrow guardrails of weather and work, politics, and sports. It makes sense in the context that a hidden purpose of banter is to prove one’s normalcy. There’s an alternative, though, especially if you find a willing accomplice. Head for the wilds of experience and observation. Talk about that phantom tingle in your elbow scar. How the morning birds remind you of the jingle from an old commercial. Bring up an unpolished idea. I’ll admit this approach isn’t for the faint of heart. It won’t always work. But when it does, it’s transportive.

“‘Do you know that in the head of the caterpillar of the ordinary goat moth there are two hundred twenty-eight separate muscles?’ … I am not making chatter; I mean to change his life.”

― Annie Dillard, Pilgrim at Tinker Creek

Offer total attention

Let’s get the obvious points out of the way: Take a break from responding to texts and scrolling on your phone. Make some eye contact. Try providing a nod of affirmation while your companion tells a story if it’s resonating with you. Small gestures like that help build a space of connection. On a deeper level — and maybe most crucially—don’t just wait for your turn to speak! Sit with what they’re saying. Consider it an offering that deserves a thoughtful response. How would you feel if you knew that during your story they were only half-listening just so they could launch their own tale already? Give the gift of acknowledgment instead of just jukeboxing your much-loved anecdote about being chased by a coyote. It’s okay to tell that story! But try to build a deeper link than just “that reminds me of…” The best conversations are not alternating soliloquies. They exist in the interplay.

Brew psychic time

It’s important to let the other person know (tacitly or overtly) you’re not rushing anywhere. That reassurance might affect what they tell you and how deep they’re willing to go. Recently, I met up with a childhood friend I hadn’t seen in over a decade. I felt bad when the donut shop I’d chosen to get coffee had an absurdly long line. I didn’t know the area well and offered to look up another place. But he told me he didn’t mind. “I’ve got nowhere to be,” he said, and I felt some inner relief, like okay, I can slow down. The grain of this time is rich and slow. We’re here.

Ride the rogue wave

Try to suspend judgment and eliminate assumptions. Instead, cultivate a radical sense of wonder. Avoid thinking to yourself: “Here he goes with another bowling story…” Instead, go with it! Find out why the heck he’s so fascinated with bowling. Maybe he knows about bowling’s surprising origin, that it was an ancient German game meant to help exorcise one’s sins, or that the pins were once called “skittles.” Maybe he has an opinion about how the gutters coddle the modern bowler or maybe someone will have a chance to invoke Robert Putnam’s Bowling Alone, a study of the decline of collective activities in American society. The point is that everyone has expertise in something. Let them take you there. When we finally get around the obstacle of our own assumption is often the moment we learn something.

Embrace the one-on-one

Yes, group conversations can be wonderful. They’re effective at bringing in more voices and creating interesting ricochets, but they can also introduce the snarls of group dynamics and politics, as well as giving folks more license to check out. A one-on-one conversation turns up the intensity. You’re on an island. You’re in a conspiracy. You can have much more of an influence over where the conversation goes, toward the recurring goat wizard character in your dreams or a nagging problem you’re having at work. There’s less threat of people talking over you or being ganged up on. There’s less pressure to conform. There’s just you and the other person. It’s a safer space to take some small risks and get personal.

Be honest

Summary is a gloss. Avoid it! Guide the other person into the weirdness of the weeds. Be real. Otherwise, what are we doing here? When you let yourself be a little vulnerable, often the other person will feel like they have permission to as well. You’ll enter a psychological room you might not have been in before together, participating in the magic of shared experience — something that happened to them happened to you, too. If you get there, you’ll marvel at it, at how much we keep locked away that others feel, too. Or it’ll go the other way, and you’ll marvel at how vastly different your paths end up being. Of course, don’t let just anyone into that room. Stand guard but lean toward taking chances. That’s the way into the wilderness.

No One You Know is forthcoming from Outpost19 on May 4, 2021. It chronicles Schwartzman’s deepest, weirdest, and most memorable encounters with strangers, all revolving around the question of what does it mean to really know someone. Preorder a copy here.

Debut book NO ONE YOU KNOW out now from Outpost19 | Founding Editor, True.Ink | Twitter: @jdschwartzman |

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