This article offers an outline of the challenges particular to intersubjective approaches to psychoanalytic psychotherapy in South Africa. It focuses on the possibility (and impossibility) of empathic inquiry and the dynamics of shame when racial difference, and all its associated baggage, dominates—for a moment or for months—the interaction of the therapy dyad. It focuses on the limits of empathic immersion when difference confers a fluid, shifting, but ever-present otherness on every encounter. It draws on the work of Allan Schore in relation to affect regulation and self-development, of Philip Bromberg on dissociation, and of Andy Morrison and Melvin Lansky on shame. The article suggests that struggles with empathic attunement in racialized contexts are often deeply affected by shame. This is associated with visceral experience of the social body, positioned by race and gender. Understanding the roots of shame experienced in therapies across racial and cultural divides marks the beginning of shared subjectivity and mutual regulation.