This paper highlights the importance of context in a therapeutic dyad. The unnamed context can be a powerful anomaly that can contribute to the perpetuation of social injustice in terms of race, power and culture, by allowing a white therapist to avoid discomfort, whilst leaving the patient of color holding the unnamed. The paper explores the contemporary self-psychological therapeutic process of a “Coloured” South African male patient, Jason, and a “White” South African female therapist, and their tumultuous process to keep fighting for empathic connection. Their therapy is located in a context that itifies, impacting the therapeutic dyad through enactments, ruptures and repairs, and parallel processes. However, a complicated Twinship provides sufficient connection, allowing them to acknowledge the contributions of their contexts to the therapeutic process and on Jason’s emotional experiences.