Abstract This article views correspondence as a cultural practice to be distin-guished from conversation or the epistolary novel, and examines the letters Isabelle de Charrière exchanged with David d’Hermenches and Benjamin Constant in this perspective. A crucial function can be assigned to the inversion of gender roles in the epistolary dynamics. Addressing the baron d’Hermenches, the young woman initiates an exchange characterized by wit and galanterie. The gender difference appears in the interplay of the images projected by the two corre-spondents: David endows his partner with masculine features; Belle, however, does not accept the portrait of the young lady as a mature man, in which she detects the gallant intentions of her correspon-dent. Nevertheless, Mlle de Zuylen maintains throughout the bril-liant exchange the unconventional position of the independent young woman tending to subvert discursive and cultural norms. Twenty-five years later, young Benjamin Constant and Mme de Charrière develop an epistolary relationship in a setting no-ticeably different from the first one. This time a correspondent pre-senting himself as an effeminate young man, passive, hesitant, prone to ennui, is looking for a partner likely to guide him. Isabelle enters wholeheartedly into his search for a sentimental education, and at-tempts to convince Benjamin not only to leave behind the ethos of the effeminate man but also to adopt the project of a gender relation-ship based on equality and reciprocity.