The author argues that the widespread affective experience of disappointment has not received the analytic attention it deserves, and that this is particularly the case for disappointedness as an outstanding feature of a way of life. Disappointedness is presented as a pathological organisation or character disorder that expresses specific unconscious fantasies and gives rise to disruptive transfernce-countertransference manifestations. The author singles out disappointedness as a special problem rather than, in the usual way, subsuming it under depressiveness or masochism and then assigning it a subsidiary or merely descriptive role. With the help of a case example, he attempts to illustrate the benefits of heightened clinical awareness of disappointment and disappointedness. These benefits include increased access to the compromise formations that can stand in the way of effective analytic work.