The concept of the holy harlot, a type of female saint defined by a youth spent in licentious sin, followed by repentance and a later life spent in an often eremitic and ascetic sanctity, may at first appear as a contradiction in terms. It implies the synchronic coexistence, within a single body, of holiness and harlotry, sin and virtue. This book will reveal that in many ways holy harlots – Mary Magdalene, Mary of Egypt, Thaïs, or Pelagia, to name but a few – are paradoxes that reflect and refract the shifting and multivalent conceptions of femininity as a whole in the medieval period, and especially as it intersects with notions of authority, holiness, and the body. Indeed, we shall see that the saintly prostitute constitutes a smorgasbord of medieval femininity, containing as she does the potential for both sin and virtue, Eve and Mary, sexual sin and virginity, youth and old age, submission and power, enclosure and geographical freedom, as well as barrenness and motherhood. Since Joan Wallach Scott memorably qualified gender “a useful category of historical analysis” that warrants the writing of a “new history,” what better way to adopt this approach for the Middle Ages than by providing the first literary history of the holy harlot, a figure that encompasses all aspects of the feminine? This book proposes to investigate the holy harlot as a category of saints in English religious literature, in texts that span the ninth to the sixteenth centuries, in Old English, Middle English, and in the French of England. The holy harlot is a particularly malleable and multivalent model, which welcomes all aspects of femininity but also comes, in the medieval period, to represent humanity as a whole and the hope for salvation through unconventional means. As such, she is an utterly relatable type of saint, most especially for women, but also for the laity, and ultimately for Everyman. Though it may appear strange to us that a male cleric should encourage, and be encouraged, to emulate the particular brand of femininity performed by female prostitutes-turned-saints, this is exactly what happens in the Middle Ages, for instance in the writings of Bernard of Clairvaux (see Chapter 2).