Having acknowledged the recurrent theme of education in Stanley Cavell's work, the discussion addresses the topic of scepticism, especially as this emerges in the interpretation of Wittgenstein. Questions concerning rule-following, language and society are then turned towards political philosophy, specifically with regard to John Rawls. The discussion examines the idea of the social contract, the nature of moral reasoning and the possibility of our lives' being above reproach, as well as Rawls's criticisms of Nietzschean perfectionism. This lays the way for the broaching of questions of race and America. The theme of the ordinary, which emerges variously in Cavell's reflections on Emerson, Wittgenstein and Austin, is taken up and extended into a consideration of Thoreau's "experiment in living". The conversation closes with brief remarks about happiness. (Contains 34 notes.)