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Numerous studies have emphasized the importance of psychoanalysis in Critical Theory. It is often asserted that authors within this tradition, seeking to understand the contradictory elements of capitalism, have approached psychoanalysis primarily from a theoretical perspective. This article highlights a significant exception to this prevailing trend: a profound and still relevant debate on transference, more precisely, the management of love, empathy, compassion, and coldness in clinical practice. Indeed, Theodor Adorno and Erich Fromm were the actors of this discussion, and, as a result, they stand among the pioneers in analyzing psychoanalytic clinical practice and its social function. In 1935, Fromm published an article in which Freud is depicted as a revolutionary figure for introducing the concept of the unconscious. This revolution is, nevertheless, constrained by bourgeois values, which inevitably shaped the goals and societal role of the psychoanalytic technique. Adorno, however, defended Freud and attempted to comprehend the critical function of the analyst's coldness. This paper concludes by underscoring the enduring relevance of this discussion within Adorno's work while also pointing to the fact that the issue of empathy remains a topic of continual debate within the realms of critical theory and the broader field of psychoanalysis.