Research on the meaning of leisure, while taking account of gender, has not situated leisure meaning within the context of age. Age is not only a biological and psychological variable but a socio-cultural and historical one as well that is likely to hold significance for leisure meaning. Hence, the purpose of this study was to explore from a developmental perspective the meaning of leisure among women and men in midlife, and if and how gender distinguished leisure meanings. In-depth personal interviews were conducted with 54-middle-aged, working and middle class, Euro-American women and men. Results indicated that the meaning of leisure in midlife is multi-dimensional and reflects: (1) the need for novelty and disengagement and (2) the age- and gender-related dialectic of affiliation and agency, expressivity and instrumentality. Suggested is that leisure is potentially not only a context for development but also an expression of development. That is, the meaning adults ascribe to leisure in midlife reflects their developmental issues and concerns. It is also suggested that gender distinctions in adult leisure are modified and perhaps even superceded by social class and parental and marital status, as well as psychological capacities of the individual. The challenge for leisure researchers and practitioners is to incorporate and account for the complex, dialectical process of adult development and leisure in leisure theory and service delivery.