Within the field of church history, this article is a study of a specific topic with regards to the Reformation period, namely, asceticism, from an uncommon perspective. One of the most well-known Reformation treatises, Martin Luther's On the Freedom of a Christian, is read in conversation with an earlier ascetic writing, Maximus Confessor's The Ascetic Life, and then compared to an understudied debate from the late sixteenth century between the Lutheran Tübingen theologians and the patriarch of Constantinople, Jeremiah II. This textually-based study is concerned both with the methodological problems that characterize the politics of comparison and with the present debates surrounding asceticism. In the end, it is argued that asceticism is not only a historically valid topic of study in a Lutheran setting, but also theologically relevant. Based on a distinction between spiritual and physical exercise, I argue that there is a social dimension to be rediscovered if inner dimensions of "piety" are reconnected with embodied, visible and communal practices in the context of the counterculture that is the Christian church.