Bereavement offers opportunities for self-growth because previous compromise formations and internalizations cannot be held against the magnitude of the trauma triggered by the loss of a significant object. Defensive positions give way under the powerful drives and needs set free by the loss of the need-satisfying object. The pressure of these drives and needs propels and compels the bereaved to seek their satisfaction. Often, unresolved conflicts and themes from childhood and adolescence are reactivated by this experience, and the bereaved person has a “second chance” for real change and growth. Sometimes this enables an in-depth treatment experience reminiscent of a good analytic patient. Other times this is not so, and the analyst's ability to be helpful remains limited. This article explores an example of each.