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This paper critically examines the relationship of psychoanalysis to science and art. Its point of departure is Michael Rustin's theorizing. Specifically, in considering the possibility of a psychoanalyst's having an aesthetic orientation, the author analyses: 1) the difficulty of there being any connection between psychoanalysis and science because science's necessarily presupposed subject-object dichotomy is incompatible with transference, which, beginning with Freud, is basic to psychoanalysis; 2) the complex relationship between psychoanalysis and aesthetics using Maurice Merleau-Ponty's philosophical perspective as well as Luigi Pareyson's theory of aesthetics; 3) the Kantian foundations of the psychoanalytic notion of art as the ‘containing form of subjective experience’; 4) intersubjectivity, without which clinical practice would not be possible, especially considering matters of identity, difference, the body, and of sensory experience such as ‘expressive form’; 5) the relationship of psychoanalysis and art, keeping in mind their possible convergence and divergence as well as some psychoanalysts' conceptual commitment to classicism and the need for contact with art in a psychoanalyst's mind set.