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In this paper, the author argues for a dynamic conceptualization of forgiveness during psychoanalysis. The trauma of failed expectations in intimate relationships is narcissistically dislodging. When legitimate expectations in relationships are not met, forgiveness becomes a challenge for ego to restore the lost narcissistic balance through the resumption of a significant internal bond. The author argues that the ending of any successful analysis is marked by three possibilities regarding the patient's relationship to significant others and his traumas: in cases where the relationship was marked by minimal expectations, one simply learns to accept the wrongdoer without ever feeling the need for forgiveness; in cases where a relationship was marked by high expectations, the patient can learn to accept the trauma without the will or need to forgive its perpetrator. However, even with the painful frustration of high expectations in an intimate relationship, the patient can come to forgive his wrongdoer if there remains enough of a positive internal bond to be salvaged. The developmental roots of such forgiveness, as well as the addictive characteristics of ‘nursing a grudge’ and the conversion of the qualitative mode of seeking fulfillment into a quantitative one, are further investigated.