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This article traces the ways that playfulness shifts and grows with the child and with the parent-child dyad. It also speaks to the paradoxical manner in which feeling essential as a parent is both necessary at the beginning of the child’s life yet must evolve into relevance as the child’s autonomy warrants. Interestingly, grace and playfulness are both a content and a process in parenting. The playful parent’s wisdom produces a sense of grace over time just as it produces a way of being that the child can internalize so that they too can eventually parent with grace and fun should they so desire.