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Departing from the observation that today’s approach to analytic exchanges is far more complex than in earlier times, this paper addresses listening, understanding, and interpreting. This paper begins by presenting the basis and utility of a theory on five motivational systems and demonstrates the need to shift from a structure-centered view to a system-centered view. The nature of communication during analysis is considered from several standpoints. This paper discusses differing views on free association, the narrative, and particularly questions pertaining to the findings of the “adult attachment interview.” The patient’s sensitivity to the presence and influence of the analyst and the analyst’s recognition of nonverbal and verbal communications are then discussed. A brief clinical example is presented to introduce a differentiated depiction of the variety of interventions that analysts employ. Throughout the paper, the author presents his views on listening, understanding, and interpreting, which are in dialectic contrast to many other analysts’ perspectives in the present period of theoretical pluralism.