Bereaved individuals often experience profound social pressure to conform to societal norms that constrict the experience of grief rather than support it. This article explores grief in Western society through an analysis of the underlying structures and values that are a part of this social system, utilizing the lens of critical theory. Critical theory examines social norms and conditions in order to identify and expose oppression in various contexts. This article examines the social rules that govern the expression of grief, the role of attachment, social pain, and shame as potent forces that promote compliance with social rules, and the ways that the underlying assumptions and values in Western society shape how bereaved individuals are expected to react. Implications for clinicians who work with terminally ill or bereaved individuals are then reviewed.