The author examines biblical characters who challenged the justice of God. He contends that these lamenters laid the foundation for the rabbinic tradition of chutzpah. They freely faced God with their disillusionment and anger. Their intimacy with the Divine is exemplary. The author acknowledges the ambiguities of God's response to despair and contextualizes lament in the case of a woman who has been sexually abused and seeks pastoral guidance. This article integrates exegesis and theology with theories of anger and intimacy.