Despite increasing recognition of the importance of multicultural sensitivity in psychotherapy, studies offering in-depth exploration of client experiences are relatively rare, and studies exploring both client and therapist perspectives even less common. This paper explores how clients and therapists experience the presence of racial identity in psychotherapy. Eleven client–trainee therapist pairs attending a free clinic in Johannesburg, South Africa, were interviewed and transcripts were qualitatively analyzed utilizing psychoanalytic research methods. This paper explores three core themes: the difficulty of talking about racial/ethnic identity; the uneasy relationship between psychotherapy and culture; and the struggle for understanding between client and therapist. This paper concludes with an invitation to embrace ambivalence, uncertainty, and partial understanding in the face of racial trauma.