The classical-Christian model of friendship has operated for many centuries from oral traditions and through the age of print. However, technological developments in communication and media rearrange mindscapes. Consequently, values, or, those things that give meaning, can change, such as perceptions of friendship. If one accepts that communication is vital to human relationships, the paradigm for the classical-Christian friendship should operate according to the new vocabulary of expanding communication and media possibilities. This work examines literature and philosophical thought within their historical contexts in order to gauge the operation of the classical-Christian friendship model from the beginning of Western literature to Western literature at the apex of print culture.