This study uses the literary metaphor of the monstrous woman to trace the construction of a particular gender ideology in English narratives of the fourteenth through early sixteenth centuries. Drawing on recent scholarship on monster theory, the rhetorical uses of medieval misogyny, and the reception of the Middle English romance, this study argues that the character of the monstrous woman functions as a self-conscious literary tool that allows authors, and audiences, to reflect on the accepted conventions of misogyny, patriarchal authority, and the romance formula itself. I analyze Middle English narratives including the early sixteenth-century translation of the prose Melusine, the Constance tale as adapted by Chaucer and Gower, and appearances of Medea in the works of Chaucer, Gower, and Caxton?s translation of the History of Jason to discover the ways these narratives use female monstrosity?in literal and figurative form?to dramatize the anxieties arising in a patriarchal society that defines the female as a slightly aberrant category of human, yet depends on her for maintenance and reproduction of the social order. In offering a close reading of these stories that draws on literary, visual, ecclesiastical, and didactic contexts, I explore the new possibilities in fiction offered by the Middle English romance and demonstrate how the monstrous women act as a powerful and multivalent literary trope: they offer their narratives a means to interrogate the prevailing gender ideology; expose the constructedness of and agenda behind existing ideological, political, social, familial, and physical spheres; challenge the currents of medieval misogyny; and fully dramatize the demands of a social order that, in Othering and ordering its female elements, makes women into monsters.