This chapter interrogates the widespread modern framing of Strozzi’s life and music through the unanswerable asking of whether or not she was a courtesan, and proposes alternative viewpoints from which and with which to understand and represent her. Working from a reception study of popular and academic cultural framings, new engagement with primary materials, and intersectional feminist perspectives on the analysis and representation of contested gendered experiences, this chapter asks what it is that this repeated question does – its functions and its fall-outs – and suggests another way of engaging with the scanty material evidence that has survived of Strozzi’s life. This chapter concludes with a proposal to retire the courtesan question in favor of a more grounded and culturally sensitive understanding of Strozzi’s family life through common seicento Venetian relationship practices, restoring Strozzi’s own representation of herself to the forefront of our representations of her music and person.