This paper is based on my experience of working in an outpatient centre for adolescents at risk in a North London borough. The paper focuses on the pressures encountered when adolescent patients want to stop treatment prematurely, and on the risks of re-enactment in the transference. Clinical material is presented from the treatment of an adolescent girl who resorted to cutting herself when she had to face new developmental stages. Her unresolved Oedipal anxieties as well as possible meanings of the nature of her self-destructive behaviour are explored. Finally I attempt to explore how my struggles with letting her go contributed to her psychic development, which has continued since the end of the therapy.