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The thesis of this paper is two-fold. First, it proposes that the psychic reality of the borderline patient evolves in a three-step process during the analytic treatment. These steps include: (i) experiencing and presenting disparate psychic states without the awareness of inherent contradictions, (ii) observing, acknowledging, and mending the splits responsible for these contradictions, and (iii) developing a capacity for feeling and accepting paradox, i.e. coexistence of multiple meanings at different levels of abstraction. Second, the author suggests that this three-step movement vis-à-vis the associative material takes place first within the analyst's reverie and then in the patient's psychic reality. The analyst's holding, unmasking, bridging and depth-rendering interventions (and the vicissitudes of identification) make the patient's advance possible. The author presents two clinical vignettes, highlighting these hypotheses and their technical implications. A vignette from the non-clinical realm of a mother's interaction with her children is also included in the hope of demonstrating a developmental ‘Anlage’ of the analyst's interventions outlined above. The paper concludes with the observation that the practising analyst also needs to traverse a ‘simplicity-contradiction-paradox’ sequence in his view of the divergent theoretical approaches to the analytic understanding and treatment of severe character pathology.