One of the central issues to which the Cappadocian fathers frequently returned was the possibility of Christian paideia. It has been pointed out that the idea of morphosis, a never-ending process of giving shape to one’s life in imitation of Christ, is at the heart of Gregory of Nyssa’s educational thinking. What has been overlooked is the way Gregory’s awareness of paideia as an engagement of the subject with an object raises the methodological problem of how this relationship can be established. This chapter illuminates Gregory’s concept of self-formation by investigating the ways in which he theorises the acquisition and ordering of knowledge suited to the life of faith. A reading of his Life of Moses demonstrates that, drawing on the rhetoric of an opposition between Christianity and classical culture, Gregory re-evaluates this tension from a pedagogical perspective. His novel idea is that the negotiation of foreignness and kinship can be a catalyst for Christian self-perfection.