This study argues for the importance of competitive discourse in placing the study of the ars dictaminis within the cosmopolitan tradition of humanistic Latin literature in the Middle Ages, particularly as it is expressed in the writing of Boncompagno da Signa and Guido Faba at Bologna in the first decades of the thirteenth century. Examining cultural links and similarities to the competitive literary culture of twelfth century humanism in France and northern Europe (especially the Goliardic poets), it also compares the function and relative prestige of ars dictaminis to other studies at Bologna, especally canon law. This comparison focuses in particular on the respective ways each discipline employs narrative fictions, and this comparison establishes the humanistic literary character of the cultivation of ars dictaminis. Ronald Witt has argued that the textual culture of Bologna in Boncompagno's day is dominated by a practical legal orientation, but this study would qualify that claim by exploring the literary copiousness of Boncompagno's writing and the literary character of several of his works, including the Rota Veneris; it likewise links this literary performance to a pattern of competitive discourse that elevates ars dictaminis above other disciplines, Bologna above other studia, and Boncompagno above other masters. The study then turns to the work of Guido Faba, especially the Summa dictaminis and Dictamina rhetorica to explore how Guido deepens and broadens Boncompagno's competitive discourse, especially through the epistolary narrative sequences of the Dictamina rhetorica.