In the first controversy between Marsilio Ficino (1433-1499) and Giovanni Pico della Mirandola (1463-1494), the Florentine Duecento poet Guido Cavalcanti is central to the argument. The dispute between Ficino and Pico over Cavalcanti’s canzone Donna me prega is therefore in this article used in an attempt to throw light upon their further disagreement about the Platonic philosophy of love. The first Pico-Ficino controversy is in part played out over Florentine poetry, but does not have poetry as its prime concern. In essence, the miniature dispute about the Donna me prega encapsulates a grand-scale conflict regarding how to live and die according to Platonic ideals. The themes of the controversy are firstly the interpretation of Plato’s Symposium, in particular Diotima’s speech, and secondly the practical conclusions one should draw from Plato’s fictional banquet. Ficino’s position is presented mainly through the seventh book of his Symposium commentary, and Pico’s counter-position from his detailed commentary on a canzone by Girolamo Benivieni’s, the Amor dalle cui, in his Commento.