Friendship with the ancients is a set of imaginative exercises and engagements with the work of deceased authors that allows us to imagine them as friends. Authors from diverse cultures and times such as Mengzi, Niccolò Machiavelli, W.E.B. Du Bois, and Clare Carlisle have engaged in it. The aim of this article is to defend this practice, showing that friendship with the ancients is a species of philosophical friendship, which confers the unique benefits such friendships offer. It is conducive to epistemic virtue, notably the related virtues of epistemic humility and of relational understanding. When we cultivate friendship with the ancients, we are not learning facts about them, but aim at understanding their views in their full scope in a way that a relationship between friends allows.