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 , 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 our own, Internet-enabled experience of communicating over distance. In so doing, it seeks to contribute towards our understanding of the ways in which information and communication technologies influence humanity by taking a long-view of many of the more radical claims for the ways in which the Internet effects change in culture, society and self. The thesis is structured thematically, with chapters examining the experience of distance and presence in these two periods, the potential for meaningful engagements by way of communicative media, the technological reconfiguration of social networks, and shifts in the public/private distinction. In its conclusions it is broadly sympathetic to the somewhat pessimistic positions of Heidegger and Borgmann, finding evidence and supplying argument to support the notion that the Internet does in some circumstances serve to diminish our meaningful involvements with the world and each other. It is, however, critical of many of the more extreme arguments for the substantive impact of the Internet, which very often lean too heavily towards naive technological determinism, neglect the social shaping of technology, overemphasise the radical novelty of the Internet, or simply deny or downplay many of its undoubted benefits. (shrink)