The digital era seems to have led to the atrophy of our ability to converse with ourselves and to empathize. Thus, in the school environment it is increasingly necessary to emphasize sharing the energy of students’ emotions, generating a climate that is highly dynamic, rich, fluid, and creative. This chapter describes a didactic activity that sees conversational agents as a key to generating engaging learning experiences, thus reconsidering and reinterpreting the traditional class period. Technology can facilitate the return to a form of learning centered around conversation itself, not only between man and machine but above all between humans. It can do this by stepping aside at the right time. To help achieve this goal, we hereby present a didactic tool for the study of Greek literature — the conversational agent “Sappho the Poet” (it. “La poetessa Saffo”), modeled after one of the most mysterious and iconic figures of all classicism.