Parenting reinforces tolerance of grief because its joys are balanced by elements of heartbreak. These challenges presented to adults by new evolving attachments create opportunities for growth. Reviewing two discussions led to the consideration of societal realities interfering with movement from archaic to mature attachments, and how culture may influence a clinician’s outlook. Therapists who don’t understand this could, as in the case example, place implicit demands on patients to separate, and unknowingly be experienced as suggesting abandonment. Thus awareness of cultural bias is central to avoiding such involuntary blindness. This applies to a clinician’s theoretical bias as well. In this regard, an intersubjective perspective needn’t be adhered to so rigidly that it invalidates singular experience, ie., that of an individual parent. The concept of adult developmental failures provides a credible theory of the origins of “defiance” and “compliance,” helping to illuminate a connection between them not evidenced in other theories.