The child’s capacity for play serves as a vital therapeutic tool as she negotiates the process of becoming her own person. This capacity can, for many of us, remain alive throughout the lifespan in the form of playfulness. Both play and playfulness are considered in this paper in their relationship to aging, with both these constructs permitting us to better live a life of grace and vitality. They are also considered in the context of parenting and, more specifically, grandparenting. The author describes five ways in which grandparenthood and playfulness are intertwined, much to the benefit of grandparent, parent and grandchild.