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.

Jason Schwartzman
Forge
Published in
6 min readMar 29, 2021

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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…

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Jason Schwartzman
Forge
Writer for

Debut book NO ONE YOU KNOW out now from Outpost19 | Founding Editor, True.Ink | Twitter: @jdschwartzman | outpost19.com/NoOneYouKnow/