The Best Conversations

After my recent flight from Maine to New York was canceled, I found myself with the bounty of six hours alone in a rental car. I considered the headway I could make in the audiobook of “Demon Copperhead,” but quickly abandoned that option for several episodes of the podcast “Conan O’Brien Needs a Friend.” I wanted company. If I couldn’t chat away the hours with a passenger in the seat beside me, I wanted to listen to other people hitting it off.

Most episodes of the show run about an hour. Conan and his sidekicks shoot the breeze for a while, before he brings on a celebrity guest for an interview. The tone of the podcast is buoyant, full of comedic bits and good-natured teasing. It’s a fizzy soft drink, fun and weird and straightforward enough that you can follow along while keeping one eye on the GPS as you navigate the traffic around Worcester.

I listen to a lot of conversation-style podcasts — interview programs and panel discussions and shows where friends sit around and talk about whatever’s on their minds. What am I looking for in these podcasts? When celebrities are in the mix, there’s the thrill of getting a glimpse into the personal life of a public figure. When an expert is interviewed, I’m hoping to learn something. But I think what I’m really listening for is connection. The shows I love aren’t the ones where a host tees up questions and a dutiful guest answers. They’re the ones where you feel like you’re eavesdropping on real people getting closer, closer to each other or closer to a conversational destination that they didn’t know they were headed for when they set out.

Conan O’Brien has been having conversations professionally for most of his career. On his late-night shows, stars came on to promote their latest film projects, and he brought enough warmth and humor and weirdness to their repartee that viewers didn’t mind that they were being advertised to. His podcast feels much more intimate. I don’t delude myself that the sweet, affectionate chat Conan had with Woody Harrelson and Ted Danson on “Conan O’Brien Needs a Friend” is identical to the one they’d have if they weren’t creating entertainment for public consumption. But somewhere outside Hartford, I found myself so thoroughly entertained I stopped doing that thing where you keep pushing the speed limit a little more, hoping you’ll be able to knock a few minutes off your E.T.A. I didn’t care how long I had to go; I just wanted to keep listening and laughing along.

I’ve been making some conversation-style audio with The Times lately, and it’s made me listen to podcasts differently. It’s made me listen to other people differently. Is what makes a conversation interesting to take part in the same as what makes one interesting to listen to? My favorite conversations with friends, the ones in which I feel most connected, are sprawling, digressive, even repetitive. They go on for hours and often fail to reach a coherent conclusion.

But they have a key ingredient in common with the podcasts that I love: presence. In the best conversations, whether they’re between you and your mom on a marathon phone call or between a professional chat host and his comedically gifted guest, everyone is listening closely. They’re curious about each other, asking what my friend Aliza calls “generous questions.” They’re reacting authentically in the moment without a script or an agenda. They’re allowing the conversation to happen without muscling it toward any predetermined outcome.