This paper reflects on the technical challenges posed to the therapist by an adolescent who finds it hard to engage in the therapeutic process. This is done through the description of a year of three times weekly psychotherapy with a 14-year-old girl who struggled immensely to begin to ‘think’ about her anxieties about sexuality and separation in her sessions. Despite seeking therapy of her own volition, and being reflective about the links between her state of mind and her family history in the assessment sessions, she remained silent for much of the time after she started therapy, only talking sporadically and mainly expressing her conflict through self-harm. The paper describes the therapist’s difficulties in delivering interpretations when confronted with the patient’s defences against having her internal experience understood. Development in the adjustment of the technique and working through the countertransference are described to show how small steps could be taken towards feeling and thinking together with the patient in the session.