The concept of grace is as complex as it is wide-ranging: it is relevant to social history and the history of religion, to mythology, theology, law, ethics, social aesthetics, art theory, and the theory of culture. The Three Graces embody a structure of giving, receiving, and returning, i.e., actions that form part of the discourse on exchanging goods and gifts, – one that is normally quite distinct from the discourse on aesthetics and art theory. The question arises: how can aspects of the grace-discourse be reformulated by means of the gift-discourse? How can we form a conceptual configuration of gift, social interaction, and art? From a wide array of possible examples, some are singled out here for closer inspection: Castiglione’s sixteenth-century model of courtly society, the connection between the social aesthetic use of the concepts of grazia and sprezzatura, and their role in art theory, as well as the enhanced meaning of these concepts in the combined discourses on love, art, and (theological) grace that are to be found in the friendship between Michelangelo and the poet Vittoria Colonna; examples from the eighteenth to the twentieth century include Schiller’s considerations on grace and Charis, giving and being gifted, as well as Nietzsche’s new morality associated with lightness and self-giving. The essay is framed by Pliny the Elder’s anecdote about the competition between Apelles, the master of charis, and his fellow painter Protogenes, and by Pasternak’s modern version of it: a short story about two rival writers and their antagonistic exchange of gifts.