Abstract When we talk about things like the 'lost art of letter-writing' or the 'digital communications revolution,' what do we mean? What do we lose and what do we gain as we move towards digital ways of being in the world? Critically engaging with many of the canonical writers in the philosophy of technology (Martin Heidegger, Albert Borgmann, Don Ihde, Bruno Latour, Hubert Dreyfus and Jürgen Habermas, for example), and following what has been termed the 'empirical turn' in that discipline, this thesis answers such questions by means of a philosophical, comparative study of epistolary technics and praxis in the early nineteenth and 21st centuries, making use of Romantic era archival letters and related materials to compare and contrast o...