Brief psychoanalytic groupwork was carried out with two small groups of youths aged 15 to 18 years incarcerated for juvenile offences. The qualitative study of a preventive group intervention for HIV/AIDS risk-taking aims to extend our understanding of, first, the meaning of HIV/AIDS and processes of HIV/AIDS risk-taking in high-risk youths and, second, the mechanisms that may moderate those processes. The specific content of AIDS representations and the intrapersonal developmental processes of human relationships found to underlie the groups’ functioning are more consistent with a psychodynamic model than a ‘rationalist’ model. Three different orientations to AIDS were identified from the intrapersonal and interpersonal patterns and the changes over the course of the sessions demonstrated the value of the groupwork in promoting movement towards greater maturity.