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The concept of regression is schematically reviewed, focusing on the complexities and confusions that have surrounded this contested notion in the course of psychoanalytic history. Clinical illustrations are used to suggest descriptive differences in regressive functioning occurring in the course of psychoanalysis. It is argued that there may be an important distinction between the sense-making (adaptational, maturational, and integrative) aims of therapeutic discourse and the distinctively deconstructive conditions of a psychoanalytic process. In this context, the “regressive” impact of the free-associative method is illustrated, and on this basis, it is suggested that there is a significant and profound difference between “free association” conceived simply as uncensored storytelling and “full-on free association” as closer to the babbling of a stream of consciousness.