This discussion is a response to Julie Gerhardt’s interesting and broad-reaching paper on libidinal and destructive envy. Gerhardt makes a valuable contribution in exploring the intersubjective roots of envy in early identificatory refusal and maternal narcissism, and in emphasizing the complexity of envy. I differ with her on several points theoretically, including her interpretation of Klein’s seminal construct and her application of social and evolutionary psychology. I appreciate her deconstruction of envy into libidinal and destructive components but question the usefulness of delineating envy into these two separate types. I discuss the clinical vignettes through a bidirectional relational lens, focusing on the intricacy of working through highly charged enactments in which patient and analyst’s inner worlds are deeply entwined. From this perspective, I understand the patient’s “envious” attacks as efforts to penetrate and reach painful and dissociated areas within her analyst in order to heal and grow.