Heterosexual romance and marriage are institutionalized ideals in our society, set forth, in part, through the portrayal of stereotyped gender roles in fairy tales, such as Cinderella, and by the mainstream media. This thesis explores the cultural messages aimed at women, which impose the necessity of altering oneself to achieve marriage, and offers feminist viewpoints. Using the form of the personal essay, I discuss the ideals of Cinderella, Prince Charming, marriage, and Happily Ever After as unrealistic, though still prevalent, given the popularity of books like The Rules: Time-tested Secrets for Capturing the Heart of Mr. Right, and Princess Diana as Cinderella icon. Essays on my own experience of marriage and divorce supplement the cultural issues, juxtaposing the personal and political toward a new paradigm for relationships.