Within the cultural context of Chinese families, when bereavement is intertwined with end-of-life caregiving, long-term relational wounds, suicide-related death, stigma in acquaintance-based communities, and internalized ideals of a “good death,” complicated grief may not primarily manifest as overt sadness. Instead, it may present as a sense of relief followed by shame, guilt, and self-judgment. This study adopts a retrospective, theory-informed single-case design. Drawing on theories of prolonged/complicated grief, suicide bereavement, anticipatory grief, the dual process model, meaning reconstruction, and self-compassion, it analyzes an early-stage counseling session and subsequent feedback from the client after bereavement. The findings suggest that the client’s core difficulty does not lie in a “lack of grief,” but rather in a complex psychological conflict shaped by the coexistence of relief, moral pressure, social evaluation, and self-blame against the background of long-standing relational injury. In such contexts, the focus of complicated grief counseling should not be to guide clients toward standardized expressions of grief. Instead, it should aim to reduce secondary harm arising from their own emotional responses and facilitate the reconstruction of relationships with the deceased, the family, and the self through a more nuanced and realistic understanding.