Individuals working long hours and/or experiencing work-related stress, including work–family conflict, are less likely to engage in health-promoting behaviors. Grounded in a life course perspective and guided by the conceptualization of life course fit, this study examined appraisals of fit between work and family roles and engagement in health-promoting behaviors, specifically physical activity and family meals, using a sample of parents (n = 811). The sample was drawn from the 2008 National Study of the Changing Workforce, a nationally representative sample of workers in the United States. Results suggest that multiple dimensions of fit were associated with greater frequency of exercise and family meals. Furthermore, parenting demands and eldercare moderated these associations. A better understanding of the proximal processes related to engagement in health-promoting behaviors would be valuable in understanding how to secure the health and well-being of families for the future.