Western cultural discourses generally deem fat unhealthy and unattractive, providing strong motivation for body nonconformists to lose weight. Semistructured interviews with 42 overweight and obese participants illuminate how individuals understand health and beauty weight-loss motivations and the relationship between the two. Interviews indicate that health and beauty motivate because they are seen as means to various ends. Specifically, participants aspire to health to fulfill various social roles and to live long, meaningful lives. Moreover, they aspire to conventional beauty ideals hoping that aesthetic conformity will elicit benefits, both psychological and social. Interviews also illustrate an intertwining of discourses in which participants conflate beauty and health in three ways: indicating that depictions of the beauty ideal are depictions of the health ideal; using beauty indicators as health indicators; and employing beauty as a motivator for health goals. This article concludes with a discussion of the health, social, and policy implications of these findings.