Why might intelligent, assertive females overlook sweet, caring guys, choosing instead to date males whose traditional masculinity makes them popular with other powerful males but who treat females and "weaker" males poorly? This lesson provides a structure for, reflection on, and critique of contemporary gender stereotypes. Students explore the history and effects of gendered sexuality, which begin at birth and continue until death. Gendered sexuality refers to the ways in which we experience our sexuality based on the interaction of our biological sex and gender socialization. The story told in this lesson illuminates how expectations for males and females are based on an historical and cultural legacy that all too often goes unexamined. We describe this legacy as an historically constructed pair of binaries, called the "Four Boxes of Gendered Sexuality: Good Girl vs. Bad Girl and Tough Guy vs. Sweet Guy." Educators may use this lesson to assist a range of populations in understanding where these expectations come from, what enforces them, and their effects on sexual attitudes and behavior.