This study analyzes the position of the father of the Italian language, Dante Alighieri, towards the ambivalence of the female figure, produced by the medieval imagination. The purpose of this writing is to show the paradox that enveloped this figure in the course of the Dark Ages and of which Dante himself is an emblem, through a study that, in addition to framing the context of the time, goes from the ‘Dolcestilnovo' to the ‘stony rhymes'. The Middle Ages is par excellence the century of the predominance of religion over reason, yet it is at this point that the theological paradox that surrounds the figure of woman appears: to which female model does the medieval world refer, that of Mary or Eve? Is the Virgin, the one who intercedes for mankind before the Creator, the representation of the medieval woman or Eve, the one who first violated God's law? The Italian writer himself represents this paradox both in the ‘stony rhymes' (anticipating the figure of the femme fatale of nineteenth-century literature) as well as in the various female figures inserted in Hell, and in the angelic figure of Beatrice. Therefore, if on the one hand the world of medieval literature presents the angelic features of the female figure, on the other it condemns this same figure in as many literary and artistic representations, up to blossom in repressive attitudes that culminate in the sad historical chapter of the court of Inquisition.