In Grief: A Philosophical Guide, Michael Cholbi characterizes grief as a “questioning attitude”; it calls attention to and prompts questions about the significance of the departed specifically to the griever. Accordingly, Cholbi assigns grief a largely self-directed cognitive purpose: grief’s goodness is that it leads—when things go well—to greater self-knowledge. In this paper, I question this claim. Calling upon an ordinary episode of grief, I argue that there are at least a few cases of grief in which greater self-knowledge is neither likely nor reasonably expected.