For the thirteenth-century Tuscan poet Guittone d’Arezzo (c.1235–94), the construction and navigation of potentially conflicting temporalities are crucial to the developing narrative of self-representation that plays out across his poetic oeuvre. Beginning his literary career writing poetry that engaged with and ironically distanced itself from the norms of fin’amor lyric, Guittone's early work both imports and undermines the tropes and apparent values of troubadour literature, particularly as it was filtered through the Sicilian School of poets centred on the court of Frederick II of Sicily. This output garnered Guittone quite a reputation and following, as demonstrated by the numerous correspondences he maintained with other poets (including Monte Andrea, Bonagiunta da Lucca, and Guido Guinizzelli) and the expansive presence of his poetry in the major anthologies of thirteenth-century Italian lyric. Guittone's oeuvre is divided into two periods of production, ascribed to Guittone d’Arezzo and Frate (sometimes Fra) Guittone d’Arezzo, respectively. This bipartition reflects the poet's own ‘midlife’ conversion (‘a mezza etate’, canzone XXVII, 6), when he joined a lay order, the Ordo Militiæ Mariæ Gloriosæ, more commonly if less flatteringly called the Frati Gaudenti, the Jovial Friars, on account of their rather convivial lifestyles. The transformation of Guittone into Frate Guittone occurs not only in name; it is self-consciously performed in his poetry through a change in subject matter (from erotic themes to moral and religious ones) and a sustained retrospective engagement with an ostensibly ‘sinful’ poetic past from the perspective of a confessional present. The importance of these timeframes in Frate Guittone's narrative is evident in both the language and the material circulation of his texts and has been foregrounded in scholarship on his work. For Frate Guittone, conversion takes place in a ‘now’ and that ‘now’ depends on a precise account of the ‘before’, one which doesn't necessarily or straightforwardly align with those texts written before his conversion moment. The temporal demands made by Frate Guittone's narrative impulses and polemical goals are not, however, straightforwardly fulfilled, neither can they be when the lyric voice and ‘now’, of the ‘pre-conversion’ Guittone remains legible in the texts composed before his entry into the Frati Gaudenti.