This book provides an exploration of the historical conditions that gradually defined subordinating symbols and conflictual values in social relations between the sexes. It reveals how snakes and the gelid eyes of Medusa—the archetypical snake-woman—have reverberated across the visual arts and written sources throughout the ages in association with negative emotions: fear, anger, scorn and shame. The outcomes and implications of the disturbing correlation between the dangerous female gaze, the malignitas of the snake and the lethal power of menstruation that have been woven through the fabric of the Western imaginary are analysed here. This analysis reveals an intriguing history of female reptilian hybrids—from the pleasing Minoan snake goddesses to the depressing Gorgon, Echidna, Amazons, Eve, Melusine, Basilisk, Poison-Damsel, Catoblepas and Sadako/Samara—and gives the reader an opportunity to explore things that never happened but have always been.