You 遊 is a crucial term for understanding the Zhuangzi. Translated as “play,” “free play,” and “wandering,” it is usually defined as an ideal, playful Zhuangzian way of being. There are two problems with this definition. The first is logical: the Zhuangzi cannot consistently recommend playfulness as an ideal, since doing so vitiates the essence of you—it becomes an ethical imperative instead of an activity freely undertaken for its own sake. The second problem is performative: arguments for playful Zhuangzi as exemplar resemble those of the logicians and philosophers who appear to come in for Zhuangzian criticism. This essay addresses these tensions by demonstrating how the Zhuangzi ambiguates the nature and value of you. Apparent endorsements of you are not freestanding, instead occurring in grudging replies of teachers to overly zealous students. In light of this recontextualization, a new version of you is offered that accommodates “non-playful” ways of being.