Entertaining Ambiguities explores the intersections of male-male sexual activities, subcultures, and coded language with classical reception, university culture, and Italian humanism. Through his excavation of a pair of Latin comedies— Janus the Priest and The False Hypocrite , written and performed by law students at the University of Pavia in 1427 and 1437, respectively—Ralph Hexter shows how these plays expand our understanding of the range of contemporary attitudes to male-male sexual behavior beyond previously studied registers, whether legal, ecclesiastical, or natural scientific. The plot of the two plays, one of which is an adaptation of the other, involves the entrapment of a priest who is eager for sexual activity with men. Digging deeply into precisely how the student ringleader of the entrapment plot persuades the priest to visit him in his rooms for an assignation, Hexter uncovers the coded language that the student uses to seemingly establish himself as a member of a network of like-minded men, convincing the priest to let his guard down. Hexter reads this coded language within his examination of the context of the plays’ performance and circulation—including careful reading of a range of Italian and Latin sources, such as Boccaccio’s Decameron , Apuleius’s Golden Ass , comedies by Plautus and Terence, and Beccadelli’s Hermaphroditus , among others. In doing so, he demonstrates how passages throughout both plays disrupt received ideas about the period’s sexual conventions and sexual possibilities. Reading against the grain against orthodox expectations, Hexter reveals the plays’ seemingly moralizing endings to be more suggestive and more ambiguous than they appear. Including an appendix presenting the first published English translations of both plays, Entertaining Ambiguities offers a new account of the history of sexuality, changing social mores, and intellectual exchange at the dawn of the Renaissance.