This essay briefly explores two developments that produced a remarkable turn in the relationship between philosophy and literature between the publication of Hume’s Treatise in 1740 and the heyday of the Romantic familiar essay in the 1820s: the socialisation of experience by Scottish Enlightenment thinkers and the impact of belletristic periodical culture upon philosophical discourse. These changes were interconnected, jointly exhibiting a swerve away from systematic epistemology and towards a form of essayism. As the literary genre of trusting intersubjectivity par excellence, the familiar essay had functioned as a vehicle for philosophical experiments in communication since the days of The Spectator. And yet, Hume’s idea of an ‘easy,’ conversational philosophy grounded in social correspondence increased the epistemological burden upon essayist beyond anything envisaged by Addison or Steele. The Romantic familiar essay inherits this burden while changing the stakes: thus, while the rewards of essaying for Hume lay in the consolidation of consensus through philosophically indifferent conversation, for Lamb and Hazlitt, they consisted in the promotion of a more limited social solidarity through the production of modes of reading receptive to the authenticity effects of singularity and transcendence.