Whether great conversation traverses easy or difficult terrain, its reward is a more poignant connection with others. But to converse well is challenging. The art of conversation lacks well-defined rules, yet places high demands on our capabilities. Perhaps it is helpful to consider philosopher Michael Oakeshott’s brilliantly concise description of conversation as “unrehearsed intellectual adventure.” In these three quick words he beautifully encapsulates the spontaneity, challenge and pleasure of this quintessentially human social interplay. To say that conversation is unrehearsed is to acknowledge that it depends on the moment. It thrives not on plans or goals but on improvisation. (Dialogue with the hope of some gain is not conversation; it is lecture, competition or interview.) There is an unspoken consensus among linguists that conversation is process-oriented, that its course cannot be predetermined. University of California, Berkeley philosopher John Searle once lamented that “conversation does not have an intrinsic structure about which a relevant This story is from Kinfolk Issue Twenty-Two Buy Now Related Stories Arts & Culture Issue 41 Mixed Emoji Is a picture worth a thousand words? Arts & Culture Issue 38 Social Work Hettie O’Brien considers the cost of never logging off. Arts & Culture Issue 31 The Newer You On starting over—and over—again. Arts & Culture Issue 26 Bob Ross Learning the art of relaxation from the master of happy accidents (and accidental life advice). Arts & Culture Issue 22 Personality Tests: A Brief History From warfare to psych wards to the workplace, Harriet Fitch Little uncovers our long-standing fascination with personality tests. Arts & Culture Entrepreneur Issue 22 Tips: Brainstorming and Contracts Whether you're brainstorming with colleagues or hammering out a contract, taking everyone's viewpoint into consideration leads to the best outcome.