This article engages the work of John Dewey to outline a pragmatist philosophy of communication that is adaptive to the undemocratic effects of extreme partisanship in belief and argument. Using his aesthetic theory, I sketch out an account of the phenomenological motions of communicative experience of self among others. I then examine the ways that partisan habits of thinking can warp our communicative activities. Drawing upon Dewey's writings on logic and ethics, I examine his account of the habits of intelligent communication. Building on this ideal, I propose “sympathy” as both a feeling and a cognitive method to decrease the pull of distorting partisan habits of reasoning in communicative situations. Linking mindful receptivity to conversational others and an explicit method of charity becomes a viable way to instill true communicative respect in democratic communicators.