This chapter focuses on Joseph Addison and Richard Steele as primary proponents of Enlightened culture in late Stuart England. Often seen now as ineffectual witnesses to the human costs of expanding commerce and imperialism, Addison and Steele were important as advocates of religious toleration, universal education, cultural relativism and hostility to extractive colonialism. Drawing a parallel between their modelling of empathetic persuasion in their periodical papers with Steele’s practice as a sentimental dramatist, I show how his playwriting sought to create national sympathy across sectarian, ethnic and ideological boundaries in order to create empathy for outsiders. This was a particularly urgent issue for Steele, who suffered all his career because he was Anglo-Irish.