This study investigated whether the types and amount of playful activity and thought exhibited from early childhood to adulthood are related to aspects of moral development, such as empathy, behavior, and reasoning. It explored whether the assertions of theorists such as Piaget, Vygotsky, and Erikson regarding the facilitative effect of games with rules and pretense on moral development could be supported in a retrospective longitudinal study. The situated conditions of social settings, outdoor settings, and technology settings for the play were also recorded. Self-report data were collected from undergraduate students at a large midwestern university in the United States. Results indicated that a number of relationships among these variables lent support to such hypotheses. In particular, early pretense and game play were related to some aspects of reported moral development at college age. The social condition was also highly related. Significant relationships among pretense and moral development were higher for females, whereas games were more highly related to moral development for males.