Stanley Cavell wondered in his memoirs whether or not his writing sought to make friends of strangers and strangers of friends. What could it possibly mean to pursue this aim? This chapter explores this question by way of a conviction Cavell shares as to the kind of community possible between a writer and their readers. Cavell’s exploration of his reticence to share his conviction, and subsequent demotion of the conviction to an exaggeration, offers a study in how far philosophy can demand the friendship of strangers and the estrangement of friends.