This essay attempts to expand the traditional model of negative countertransference by giving it a Lacanian twist. The author uses theories and concepts from Freud, Winnicott, and Lacan in order to explore the affective dimension of countertransference in two cases of trans-identified patients. In the first case, the author shows that wanting to do good was counterproductive, while in the second vignette maintaining a position of neutrality allowed the author to go beyond fear and pity, which led to a dynamic resolution.