Placing in parallel Fernando de Rojas’ La Celestina, Chaucer’s Troilus and Criseyde and Shakespeare’s Troilus and Cressida, one can find resonances in these works’ parody of the courtly triangle (the lovers, the go-between) and their representation of a disenchanted world. In Medieval and Renaissance Europe, the image of the seductive woman can also be related to the iconographic themes of the Three Ages of Woman and Death and the Temptation of Saint Antonio (Hans Baldung, Hieronymus Bosch, Pieter Huys, Joachim Patinir), which mingle the sacred and the profane, the erotic and the morbid. Beyond tragic overtones, Chaucer celebrates both earthly and spiritual love in his famous retraction, while Rojas and Shakespeare highlight the grotesque and the satirical.