In this essay, I work with transference, as a relational dynamic from psychoanalysis, to analyze love and loss experienced through learning relationships. Transference is the unconscious transfer of emotions from past relationships to present experiences. I explore transference in learning by disclosing my case study of dyadic learning, guided by Indian scholarship about a guru–shishya, or teacher–student, relationship of hierarchical, processual learning. I discuss the significance of transference for analyzing emotions of this superior–subordinate learning dyad, through my experience of transferential loss. I conceptualize transferential loss as emotions that accompany the loss of a formal, unequal, time-bound teacher–student transference relationship. I analyze this loss by scrutinizing shifting authority dynamics that I encountered with a loved academic guide, or guru. Through surfacing changes in transference and the pain of losing the teacher–student learning, this essay challenges neoliberal approaches to higher education that valorize instrumental and disembodied goals. Transferential loss connects Indian psychoanalysis about dyads and transference to management learning scholarship, including the importance of the unequal guru–shishya conceptualization for critical management education. This essay contributes to psychoanalysis in management scholarship, develops the concept of transference for learning contexts, and offers a case analysis to the management literature on grief, love, and academic self-disclosures.