This study explores the use of role play as an educational medium in order to enhance life skills amongst orphaned and abused teenagers living at a shelter in Berea, Johannesburg, South Africa. The study advocates an Action Research approach for the case study that deals with life skill development. Life skills are those abilities that help promote mental well-being and competence in young people. Life skills, this study argues, empower young people to take positive action to protect themselves and promote health and positive social relationships within the context of HIV/Aids. Role Play is observed as an educational medium and theoretical construct. This study argues that because of role play’s experiential and participatory nature, it is the most appropriate methodology to apply in the development of life skills amongst vulnerable adolescents. Role play acts as a safe dramatic metaphor for young people to practice role adoption and role flexibility. The study concludes that such methodologies should be consistently used in the educational activities run by institutions like orphanages, children’s homes and shelters, particularly those concerned with vulnerable young people.