Renaissance thinkers affirmed that also in terms of justice and friendship the relationship between the human couple reflected what it was that held together the citizens in the city. This chapter examines the immense importance of thinking about friendship and love for political reflection, and it shows the relationship of civic concord and friendship with the domestic sphere, and particularly with the conjugal relationship. This chapter studies early modern commentaries on Cicero’s De officiis as well as celebrated works of the ‘civic tradition’, namely Leon Battista Alberti’s Della Famiglia and Matteo Palmieri’s Della Vita Civile, showing that the learned Aristotelian tradition we have so far studied found its echoes also in the Ciceronian tradition as well as in the volgare. These commentaries and vernacular writings serve as part of the context necessary to understand more fully Niccolò Machiavelli’s thought on family, friendship, and sociability, which has so far not found adequate attention in historical scholarship. Re-examining some of the ways that Machiavelli constructed masculinity and femininity, and setting them into their intellectual context, this chapter aims to show that Machiavelli’s political thought was characterised by a remarkable openness towards the idea of women as dominant agents in the political sphere and by a sense of what we can term, in a postmodern manner, ‘fluidity’ of gender conceptions, in which ‘biology’ was certainly no determining factor. The chapter thus contributes to the question of the nature of Machiavelli’s stato.