Relentless hope is a stance to which we desperately cling in order not to have to feel the pain of our disappointment in the object, the hope a defense against grieving; our relentless outrage is the stance to which we resort in those moments of dawning recognition that, despite our best efforts and most fervent desire, the object of our intense desire might never be forthcoming after all; and our relentless despair is the stance to which we retreat when our hearts have been shattered and it hurts too much to do anything but withdraw from the world – and, even, from life itself. The masochistic defense of relentless hope, the sadistic defense of relentless outrage, and the schizoid defense of relentless despair all speak to our refusal to confront – and grieve – the limitations, separateness, and immutability of the object. Psychodynamic psychotherapy offers patients an opportunity, albeit belatedly, to grieve their early-on heartbreak – in the process transforming the defensive need to hold on into the adaptive capacity to relent, to forgive, to accept, to separate, to let go, and to move on. Realistic hope arises in the context of surviving disappointment… Clinical vignettes will be offered that highlight the translation of theory into practice and demonstrate the use of “disillusionment statements” to facilitate the grieving that needs to be done in order to transform relentless pursuit of the unattainable into sober, mature acceptance.