This chapter highlights the intimate connection between mourning and forgiveness, the dovetailing, and at times the interchangeability of the two constructs within the exquisitely well suited clinical arena of psychoanalysis. The most important feature of the dynamic conceptualisation of forgiveness is the emergence of the unconscious wish to forgive in the transference in order for the patient to contend with the limitations and shortcomings of a disappointing significant relationship. I demonstrate that in clinical situations genuine forgiveness has a very narrow definition, one that is dynamically imbued and a formidable challenge for the psyche. As Prager (2007) aptly observes, even though forgiveness is about the past, it has to occur in the present, in a setting designed for it and the analyst plays a central role. Invoking Freud (Freud, 1912) in The Dynamics of the Transference, Prager interpolates what Freud had to say about the patient’s illness—that just as it is impossible to destroy anyone in abstentia or in effigie, “when all is said and done, it is impossible to forgive anyone in abstentia or in effigie. If forgiveness is to occur, it is the analyst, by the analysand, who must be forgiven. And therein lies the treacherous terrain of analysis” (Prager, 2007, p. 10).