In 'Theologizing Friendship', the author aims to revitalize Jean Leclercq's defense of monastic theology, while expanding and qualifying some of the central theses expounded in Leclercq's magisterial 'The Love of Learning and the Desire for God'. The current work contributes to a revised and updated status quaestionis concerning the theological relationship between classical monasticism and scholasticism, construed in more systematic and speculative terms than those of Leclercq, rendered here through thelens of friendship as a theological topos. The work shares with Ivan Illich's 'In the Vineyard of the Text' the conviction that the rise of the Schools (Paris, Oxford, etc.) constitutes one of the greatest intellectual watersheds in the history of Western civilization: where Illich's ruminations are largely philosophical and particularly epistemological, the author's are theological and metaphysical. In his novel proposal that within the monastic and scholastic milieux there obtain parallel threefold analogies among friendship, reading, and theology, the author not only offers an original contribution to current scholarship, but gestures towards avenues for institutional self-examination much needed by the contemporary - modern and postmodern - Academy.