Two case studies describe how two women, enrolled in an undergraduate course on play, were guided to examine play across their lifespan, critique the barriers that led to a decline in their play from childhood to young adulthood, and engage in cycles of documentation, dialogue, and analysis of their adult play experiences in order to discover pathways to reclaim play in their adult lives. Two assignments were used to facilitate the students' learning process; online blogs and digital lifespan play portfolios created on interactive wikis. Research on women's leisure and feminist poststructuralism informs discussion of the findings. Implications of the study's findings suggest that supporting early childhood professionals to develop as child advocates able to articulate the value of play for children's learning and development should begin by helping them to make important discoveries about the role of play in their own lives.