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This paper explores some of the ways in which sexuality can intrude into the psychotherapeutic relationship and present both opportunities and risks to our work with adolescents. It highlights some of the complexities of this area of the clinical encounter, exploring the particular difficulties encountered by both patient and therapist when sexuality emerges in the transference and countertransference. While we are well aware of the centrality of sexual development during adolescence, far less has been written about the way in which sexuality and the erotic transference emerges and impacts on both patient and therapist. Given the profoundly unsettling nature of this area of work and its capacity to disrupt our thinking and psychic equilibrium, it is easy to underestimate how much we are drawn to avoid, negate and defend ourselves against registering such experiences. Through the discussion of clinical material with two adolescent patients, this paper explores some of these dynamics, addressing some of the technical dilemmas that frequently challenge us in this area of work. These include questions about whether and when it is therapeutically important and effective to take up and interpret the emergence of sexuality more directly in the transference and some of the risks to our patients when we ‘play safe’ and fail to do so. Most importantly, this paper aims to facilitate further thinking and discussion about an important but uncomfortable and easily neglected area of our work.