This article presents a literary analysis of the extant poetic prologue to the Hebrew adaptation of Celestina, written in Italy by Joseph ben Samuel Tsarfati at the beginning of the 16th century. The prologue is shown to be a product of various literary traditions, and an indication of the nature of the role of secular literature within the Jewish literary corpus. The poet reconciles and juxtaposes his literary inspiration, Celestina, and secular literary conceits with the conventions and character of Medieval Hebrew literature