Therapies for grief and loss have traditionally focused on the work of grieving. The goal was to reach an endpoint, now popularly called closure. There are, however, many people who, through no fault of their own, find a loss so unclear that there can be no end to grief. They have not failed in the work of grieving, but rather have suffered ambiguous loss, a type of loss that is inherently open ended. Instead of closure, the therapeutic goal is to help people find meaning despite the lack of definitive information and finality. Hope lies in increasing a family’s tolerance for ambiguity, but first, professionals must increase their own comfort with unanswered questions. In this article, the authors, one a poet, the other a family therapist and theorist, offer a unique blending of theory, reflection, and poetry to experientially deepen the process of self-reflection about a kind of loss that defies closure.