The book traces these two distinct categories of heroines as they make inroads into the preserve of male domination, and examines the various defenses male writers and artists used to slow down the pace of female emancipation both sexually and socially. Along the way, the book looks at the way in which the 1893 Columbian Exhibition in Chicago unexpectedly encouraged further female advancement, how Wagner’s operas gave women greater confidence toward self-fulfillment, and how Otto Weininger’s outrageous teachings managed to stem the tide of American female emancipation for a short time. The book surveys how the appearance of the Gibson Girl, the bicycle, and even the advent of bloomers were depicted in literature and supported the advent of this New Woman until she was grudgingly accepted despite philosophical warnings that the female agenda included a plan to destroy masculinity and make men subservient to the female rule. The book concludes with a discussion of F. Scott Fitzgerald’s The Beautiful and the Damned where the reader observes the complete destruction of the decadent-inclined Anthony Patch by a siren with no heart or introspection.