Social engagement is theorized to promote health, with ages 55 to 75—what some call “encore” adulthood—potentially being a time for ongoing engagement or social isolation. We use the American Time Use Survey (N = 11,952) and a life course perspective to examine associations between paid work, resources, relations, and healthy time use for men and women in the first (55–64) and second (65–74) halves of the encore years. Work limits sufficient sleep (full-time working men) and television watching (all workers) but also time spent in physical activity (full-time workers). College-educated and healthy encore adults—across age and gender divides—are more likely to exercise and watch less television. Marriage and caregiving encourage socializing and limit television watching, despite differential effects on physical activity and sleep. These findings fit well with a gendered life course perspective suggesting socially patterned (by work, resources, relationships, gender, age) health behaviors.