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This article deals with critical psychic transformation in a schizoid personality disorder that evolves in an object relations psychoanalysis in which “developmental mourning” plays a central role. Within a mourning process that allows for the grieving of loss related to arrested separation-individuation development, the analysand confronts the existential grief of regret that had always unconsciously haunted her. The unconscious guilt related to the existential grief of regret had caused much dissociation of self-experience and affect states. The analysand acknowledges her own part in the destruction of primal and current relationships after the traumatic impact of her early life is understood. This allows her to repair current relationships, both within her internal and external worlds so that she can open to capacities for love and creativity. The analysand's courage to consciously grapple with her regret (loss and guilt combined) allows her to relinquish self-sabotaging character defenses such as contempt and emotional withdrawl. Consequently, a second marriage is salvaged and enriched, and the analysand's relationship with her two children is dramatically improved.