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Compassion, as scholars have long noted, is one of the central themes of Boccaccio’s Decameron. Indeed, it would not be an exaggeration to say that the Decameron is one of the precursors of modern sentimentalism and the emphasis on the social value of compassion, central to the thought of thinkers from Rousseau to Martha Nussbaum. Yet while exalting the merits of compassion, Boccaccio’s works, as this paper will argue, also repeatedly probe the possible perils of this emotion. Looking at Boccaccio’s Filostrato and several of the tragic tales of the Decameron, this paper will demonstrate how Boccaccio’s fictions explore situations in which compassion leads protagonists to act too leniently or empathize with the wrong models. Rather than simply eliciting compassion, Boccaccio’s tales, in this respect, urge the reader to withhold automatic identification with the sorrow of another and reflect critically on the proper way to respond to suffering.