Conversation is one of the most mundane events of human life, yet the conversations we have can vary a lot. Some proceed only with great effort, while others engage us thoroughly. Drawing on Dewey’s aesthetics, this paper argues that the movement and rhythm of conversations can make them into genuine candidates for an aesthetic status. The key term of the paper is interaction. For Dewey, all experience, aesthetic experience included, is constituted by an interaction between humans and their environment. In his later philosophy of language, which is critical of conventionalist explanations of language, Davidson, in turn, offers a very rich account of the interactions conversations can involve. He cites the novels of James Joyce as an extreme example of just how intricate the forms of linguistic interaction can become. Though the notion of aesthetic experience does not figure in Davidson’s account, his analysis of the conditions for successful communication can nevertheless be seen to shed light on those features of conversations that explain Dewey’s interest in their aesthetic dimension.