As psychoanalysts we have grown used to thinking of our patient’s problems as rooted in past relationships and attachment patterns. We try and focus on the conflictual and traumatic events of our patient’s formative years and relate them to the current difficulties that bring them into treatment with us. However, where severe or recurrent trauma has led to a sense of dread and hopelessness with regard to the future, we also confront the death of the patient’s desire and the complex and intertwined relationship of desire, shame, and parental abuse and/or neglect. This death of desire takes us to the heart of the transference/countertransference configurations, and moves us gently from our exploration of the past into the subjunctive, “would that I could” of the present therapeutic relationship. This paper will focus on (1) the relationship between desire and shame, (2) the way in which the subjunctive constitutes and contains mourning, and (3) the relationship between mourning, hope, and psychoanalytic imagination. An extended clinical example will be presented.