In this article, Judy Blore argues that grief provides a striking case for how human weakness, disheartenment, and willfulness converge. Blore focuses on the acting out that often erupts in the context of loss and sorrow. In working with teens who grieve, we must remember key principles: grieving is natural and painful; it is hard and lasts a long time; and it brings occasions for disobedience. How should parents or caregivers handle disobedience during periods of grief? Blore gives practical suggestions, but also reminds that specific grief counseling may be necessary.