In this essay, Leonard Waks examines John Dewey's account of listening, drawing on Dewey's writings to establish a direct connection in his work between listening and democracy. Waks devotes the first part of the essay to explaining Dewey's distinction between one-way or straight-line listening and transactional listening-in-conversation, and to demonstrating the close connection between transactional listening and what Dewey called “cooperative friendship.” In the second part of the essay, Waks establishes the further link between Dewey's notions of cooperative friendship and democratic society with particular reference to machine-age technologies of mass communication. He maintains that while these technologies provide the means for extending communications throughout modern industrial nations, they simultaneously undermine the conditions fostering face-to-face listening-in-conversation. It remains an open question, Waks concludes, whether new educational arrangements incorporating interactive digital communication technologies will embody and promote transactional listening-in-conversation and revitalized democratic community.