This paper explores the roles of sexuality and gender in conflicts within fifteenth-century Florentine families by analysing the dispute between Clarice Orsini (the wife of Lorenzo de’ Medici) and Angelo Poliziano in 1479. Historians have generally framed this incident as the inevitable result of irreconcilable differences between a stubborn humanist tutor and a devoutly Catholic mother, but this neglects the unspoken assumptions that Clarice, Poliziano, and their contemporaries would have had about the erotic politics of the situation. This brief episode of Medicean history provides a fascinating case study for the ways in which homosocial relationships could disrupt family life. By analysing letters and poetry, this paper utilises the methodologies of emotions history and queer history to problematise current understandings of Renaissance Florentine families and reframe a well-known narrative in Laurentian history.