Psychoanalytic accounts of gender variant patients in the literature are rare. Psychoanalysis with these patients suffers from historical biases that determine short-sighted and pathologizing interpretations of gender diversity. This contribution provides an account of a long-term psychoanalytic psychotherapy taking an open and affirmative approach to gender reassignment. The patient was a trans adult woman, Paola, during the crucial years preceding her decision to undergo gender reassignment surgery. Through the analysis of the patient's identifications and dreams, the psychoanalytic report focuses on the developmental process of her transition path. The study illustrates Paola's psychological functioning and the therapeutic relationship, drawing on both clinical descriptions and empirical measures of Paola's personality and transferential and countertransferential patterns in the therapeutic relationship at different stages of treatment. The results show the benefits and complexities of psychoanalytic treatment with gender variant patients, during key stages of their transition journey.