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Psychoanalysis and meditation not only compensate for the other's blind spots, but also, when practiced together, can provide a richer experience than either discipline pursued alone. After considering the way meditation cultivates heightened attentiveness, refines sensory clarity, lessens self-criticism, and increases affect tolerance, thereby deepening psychoanalytic listening, I'll examine how psychoanalytic perspectives on unconscious communication and meaning illuminate and transform the nearsightedness of meditation, aiding therapists and clients in understanding troubling thoughts, feelings, and behavior. This helps therapists deepen their capacity to help those people with whom they work. The paper also attempts to illuminate how the therapeutic relationship, conceived of in a freer and more empathic way—as the vehicle for both validating a person's experience and providing opportunities for new forms of relatedness and self-transformation—provides a crucible in which old and dysfunctional ways of caring for oneself and relating to other people emerge and new patterns of self-care and intimacy can be established. In the concluding section, I will delineate meditative psychoanalysis, my own integration of meditation and psychoanalysis. Clinical material will illustrate my theoretical reflections.