The ideal of ‘conversation’ recurs in modern thought as a symbol and practice central to ethics, democratic politics, and thinking itself. Interweaving readings of fiction and philosophy in a ‘conversational’ style inspired by Stanley Cavell, clarifies this lofty yet vague ideal, while developing a revitalizing model for interdisciplinary literary studies. It argues that conversation is key to exemplary responses to sceptical doubt in ordinary language and political philosophy – where scepticism threatens ethics and democratic politics – and in works of British fiction spanning from Jane Austen through Ali Smith. It shows that for these writers, conversation can shift attention from metaphysical doubts regarding our capacity to know ‘reality’ and other people, to ethical, democratic, and aesthetic action. The book moreover proposes – and models – ‘conversational criticism’ as a framework linking literary studies to broader political and ethical commitments, while remaining responsive to aesthetic form.