This paper describes a technique using photographic portraits in medical education to encourage close observation, cultivate empathic curiosity, explore learners’ values and beliefs, and to reveal and reflect on fundamental biases. This new and evolving educational method uses the lens of psychotherapy to explore learners’ experience of the portrait in a similar way we would discuss a case in psychodynamic supervision. Through close looking and small group engagement, the facilitator creates a space for deeper reflection and collaborative exploration of the therapeutic relationship, with emphasis on countertransference and the role of prior expectations. The exercise strengthens dialectical thinking through perspective-taking, challenging implicit assumptions and fostering cultural humility. Radiologists are taught to look in every corner of the X-ray and to observe each shadow, all while evaluating the entire image. Portraits can be examined in the same way, looking for subtle clues to the personality and history of the subject. Information from other sources confirms, or sometimes profoundly changes, our evaluation. In this example, we use a historical photographic portrait to demonstrate ways of engaging medical learners as they discover common psychotherapeutic approaches. The method has the potential to enhance therapeutic encounters, improve analytical skills and reduce bias.