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Our conversation took a few side trips down some off-topic tributaries (like growing up in Nyack, New York; teen fights; and more) before we got to the subject at hand — the how-tos and why-it’s-worth-its of having an aimless conversation — but as Daniel Menaker, author of A Good Talk: The Story and Skill of Conversation (Twelve Books, $20), points out: “Sometimes the best things are in the shadows.” Menaker says aimless conversations are a bit of an “endangered species.” While the reasons to put them on the protected list are numerous, one of the loveliest, which he writes of in the book, is that since “a good conversation always involves finding common ground, it means that differences will have to retire to the sidelines, at least for a time.” And, personally, he says, some of his “sweetest times” have been spent in seemingly purposeless conversation. Here, a conversation about conversation.

How can people, in this driven-with-purpose age, retrain themselves to have aimless conversations?
If you purposely make time to have a conversation, you’re almost defeating it to begin with because you’re giving yourself another thing to do — which is sort of not the point. It’s more a change in attitude. A greater openness.

Even on an airplane? Should people open themselves up to the seat-mate conversation?
I think people deserve and ought to give themselves the luxury of daydreaming. [But] I have this theory [for conversation]. It’s not, “Who are you? What do you do?” It’s not a direct invasion of someone’s boundaries. It’s, “Have you ever been to Barcelona?” — if that’s where you’re going. If that does work and both people are willing to have a conversation, the most important thing is to be extra alert and to be able to end them comfortably.

My bad habit is that I’m an interrupter. What are some of the greatest pitfalls and remedies for people attempting conversation?
I don’t think [interruptions are] so bad. I think people are much more tolerant of interruptions than common-manners books would have it. It shows energy and enthusiasm for the topic. You take it as a form of engagement if it really is to the point.

Less easy to deal with is saying something that is offensive. The best thing to do about being affronted is be stoical. If there’s some reason you really can’t tolerate what was just said, I think you have to say something. You have to remember not to go to certain places until you’re invited. Being in a conversation is like a dance: If you don’t know what to do and you don’t feel confident taking the lead, then let the other person take the lead. That’s by far the best advice I have.

Models Of Conversational Comportment


While Menaker says a person’s favorite conversationalist is a very personal thing, there are some people in public life worth modeling your own talking points after. His own MVP of chatter was Brendan Gill, The New Yorker’s theater critic. “Even though he was quite a personage about town, he would listen and add something of his own,” Menaker says. Three others to watch:

Bill Moyers
“He follows questions but never minds going off on a tangent.”

Terry Gross of NPR
“She can be very provocative.”

Barack Obama
“He can be extremely improvised and sort of a wise guy.”