The Zhuangzi offers two apparently incompatible models of bereavement. Zhuangzi sometimes suggests that the sage will greet loss with unfractured equanimity and even aplomb. However, upon the death of his own wife, Zhuangzi evinces a sorrow that, albeit brief, fits ill with this suggestion. In this essay, I contend that the grief that Zhuangzi displays at his wife’s death better honors wider values averred elsewhere in the text and, more generally, that a sage who retains a capacity for sorrow will be better positioned for the robust joy so often identified as central to the Zhuangzi’s vision of flourishing. The sagely figures who entirely forego sorrow, I argue, achieve equanimity only through a sacrifice of the emotional range and responsiveness necessary not only for grief but also for the delight Zhuangzi recommends.