Five paradoxes of masochism are presented delineating intrapsychic and interpersonal patterns in which pain and unpleasure, rather than being simply warnings, actually seem to become aims. Elements of the apparent contradictions inherent in masochistic disorders and some of their transference and countertransference implications are discussed. The five paradoxes presented highlight: (a) intrapsychic conflict around issues of drive and defense; (b) conflict between autonomy and gratification through depending on others; (c) pain inherent in the quest for perfection; (d) pain associated with attachment to the object; and (e) pleasure evokes physical pain and injury, a screen for early dire physical trauma. Case material illustrates each paradox.