The Czech author Milan Kundera, one of the most famous contemporary “literary analysts”, is recognized as a master story-teller of the relationship between men and women. In this article, Kundera’s perspective is compared with the Lacanian statement that “there is no such thing as a sexual relation”. In a critical way, some of Kundera’s protagonists (Tomas, Klíma, Martin and Havel) are confronted with the Freudo-Lacanian interpretation of the Don Juan character. Through a short historical review, the author examines how Don Juan has evolved through the centuries from vulgar libertine to romantic hero. Kundera’s characters are situated within this evolutionary continuum. Both from a phenomenological and a structural viewpoint, a clear distinction is made between the characters of Don Juan and Casanova. The question is whether Kundera’s characters are Don Juans or Casanovas.