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In this paper, Andrea Fiore sketches the notion of familiarity in Dewey's thought, particularly in its relations with education, aesthetics, and art. The importance of that notion emerges in Dewey's well-known writings such as "How We Think," "The School and Society," and "Art as Experience," where he shows that not only does familiarity play a fundamental role in our lives, but it also constitutes a helpful tool to make our experience deeper and richer. This is particularly evident in two aspects or functions related to familiarity: recognition and interpretation. For Dewey, especially the latter has an educational value through aesthetics and art, because it allows us to activate the peculiar capacity of human beings to transform the quality of experience.