This chapter explores the idea of the gift found in the classical writers and philosophers most widely read in central medieval Europe. It explores the explicit philosophical and moral treatments of generosity found in Seneca’s De beneficiis and Cicero’s De officiis, as well as the role played by gifts in literature, from Virgil’s Aeneid to the poems of Ovid. The chapter concludes by looking at how classical ideas about generosity were taken up by early Christian writers.