In the classic tale Rip van Winkle by Washington Irving, the story of a man that sleeps through the American Revolutionary War is presented. Yet while the story is intended to be a work of humor, Irving also works to present the war of the sexes as manifest in the conflict between the character of Rip van Winkle and the various female characters that van Winkle encounters within the story. This paper investigates the gender roles in this story.