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Abstinence-only sex education is based in part on the premise that parents are their children’s best sex educators. In-depth interviews with 40 mothers of teenagers suggest, by contrast, that these mothers experience numerous challenges around talking to their children about sexuality. In this paper, I examine three of the most common barriers in mothers’ accounts of “the talk.” First, mothers perceive their teenagers as highly resistant to these conversations. Second, they experience embarrassment and discomfort around talking to their teens about sex and sexuality. Third, they expressed ambivalence about when, what, and how much to say to their children about these topics. I argue that these obstacles are shaped by cultural anxieties and contradictions around parenting, sexuality, and adolescence that are fueled by debates, policies, and programs over the past 30 years that have promulgated a danger …