Marriage is a rite of passage in U.S. culture influenced by fairy-tale expectations presented in the media and perpetuated through gender role socialization. Our study tested endorsement of marriage myths and benevolent sexism as predictors of engaged heterosexual college women’s premarital relationship outcomes and psychological well-being. Women in heterosexual relationships (N = 99) completed an online questionnaire 6–12 months before their wedding. Results indicated endorsement of marriage myths predicted positive experiences, whereas benevolent sexism predicted negative experiences. However, several interactions indicated that women who rejected marriage myths but endorsed benevolent sexism showed more negative patterns including lower relationship satisfaction and confidence, lower educational expectations, and higher depression. Results are interpreted using self-discrepancy theory such that when actual and ideal experiences are congruent, higher relationship satisfaction and more positive well-being results, whereas discrepant actual–ideal experiences predict dissatisfaction and more negative well-being. These results have implications for counseling couples on holding realistic expectations for their romantic partners. Marriage counselors can advise couples about the potential negative consequences of endorsing benevolent sexism. Exposure of common myths or unrealistic expectations about one’s partner and relationship may decrease the real–ideal discrepancy and increase marital satisfaction, thus increasing the likelihood of relationship longevity.