This paper explores questions relating to class differences between patient and analyst and how they might be addressed in the therapeutic dyad. A literature review indicates that a longstanding gap in discussions of social context for psychoanalytic endeavors is beginning to be addressed. The author suggests that issues of shame and envy, on the part of both patient and analyst, can lead to impasses and compromise treatment. Two vignettes are offered in which class differences intersect with more intimate aspects of intersubjective relating. The author employs self-disclosure as a way to foster genuine dialogue regarding the disparities that can impede our work as healers.