Current multidisciplinary research on addictions generally endorses the impression that addictive behavior is either caused or at least maintained by the external psychoactive substance. While the latter is considered to being “addictive in itself”, the psychological, experiential dimension in addictions is rendered as something secondary. However, in order to understand addictions comprehensively, the psychological dimension of addictions must be elaborated in its own terms. The present article engages in a detailed examination of the psychological, phenomenological, and psychodynamic aspects of addiction. It argues that, psychologically speaking, addictive behavior is owing to deficiencies in affective self-regulation and emerges as a compensation for these deficiencies. By tracing the patterns of addiction back to deficiencies in affect regulation, and by dealing with these deficiencies in terms of ambivalence and transitional object relations, the article suggests that addictive behavior can be understood as a maladaptive modification of responding to affective plight. The article argues that addictive behavior is motivated by the sense of being out of control. The tragedy of the addict, however, is that he only manages to replace one sense of uncontrollability with another.