Inspired by Aristotle and Goffman this article considers how the study of virtue acquisition may be pursued through an observational theorising about social interactions in institutions. Adapting Goffman's and Harré's notions of moral order and moral career, it proposes character education to be a dialogic process requiring negotiation between social actors over time. Taking part in educational institutions, learners learn to perform various roles in a manner by which virtues are to be attributed. But this is not all. Goffman's and perhaps Aristotle's accounts are arguably too 'thin' to allow for moral change, unless these processes themselves are mastered by learners and may be transcended by them. It is thus by applying the sociological imagination to the institutions we are in, the criticality necessary for true character is developed. The role of sociology in character education is therefore twofold: to inform educators in the creation of institutions and practices that transmit and manifest virtues; and, as an essential part of a virtue-ethics curriculum--giving moral agents the sensitising concepts necessary to understand, negotiate and mould the social frame.