<p>Qui (who), quid (what), ubi (where), per que (why), quoties (how much), and quomodo (how)? What could be regarded as a checklist for plotting a narrative is in fact the standard casuistical questionary for priests when judging the severity of a confessed transgression. On the threshold of the Middle Ages and Renaissance, casuistry becomes a veritable epistemology that permeates every realm of life. The often far-fetched “casos” presented in casuistical manuals not only enhanced the psychological abilities of confessors. The pastoral monitoring and the confessional inquiry into the details of the sins commited stipulated soliloquies to prepare for the act of penitential purification. This cultural practice fostered self-awareness and thus, the process of subjectivation. The first Jesuit manual for confessors was published in 1554, coinciding with the anonymous ur-picaresque novel, Lazarillo de Tormes. Traditionally discussed as a “counter-genre” to idealizing forms of literature, it also represents the first self-narration in Spanish literature. On the other extreme of literary imaginary we find the life-story of Teresa de Ávila (Libro de la Vida, 1566/1588) who has certainly a more privileged relationship to the realm of eternity, yet sometimes provides quite worldly insights in her life story. Bringing together these quite different first-person narrations and casuistry will provide new paths for understanding Spanish literature during its period of unsurpassed creativity and production.</p>