Gregory of Nyssa’s earliest treatise, the De virginitate (371), has generated considerable debate in recent decades for its elevated praise of celibacy and expostulations against marriage. Various commentators (Michel Aubineau, Michel René Barnes, Peter Brown, Mark Hart, Janet Soskice, Valerie Karras) have regarded his apparent advocacy of celibacy as ‘ironic’ (Hart), fantastically idealistic (Soskice) or a reflection of personal tragedy (Barnes). What has been overlooked in these studies, however, is the centrality of the theme of maturation in Gregory’s moral theory. It is the burden of this paper to argue that, for Gregory, the demands of the ascetic life are shaped by and adapted to one’s life circumstances and moral maturity – a theme of rich significance first enunciated in the De virginitate then later developed seriatum over his literary career. In this paper, I shall proceed in two steps. Firstly, I shall examine the trajectory of argumentation in theDe virginitate to reveal how hyperbole is used as a rhetorical strategy to encourage the reader to inhabit the middle ground between excessive rigorism and libertinism. Secondly, I shall consider the examples of physical youth and moral immaturity as ‘particulars’ that affect the decision to marry or embrace the celibate life – with allusions to texts from Gregory’s later writings for the purposes of comparison and elucidation. In doing so, I shall show that Gregory does not issue a blanket summons to virginity or to marriage, but adjudicates the appropriateness of each according to the contextual particularities of the individual.