Teenagers engage in an expanding variety of interpersonal contacts with increasing independence from the family. One aspect of this developing social realm is confronting conflict. Conflict situations are useful in assessing adolescent social abilities. Using conflict resolution role play, vignettes, and self-report surveys of 450 New York City sixth graders from 42 city middle schools, this study examined associations between adolescents’ conflict resolution efficacy and social skills. Results of the study provided insight into the use of role play measures for assessing adolescent social skills. Social skills and conflict resolution are discussed in terms of cross-context similarities and differences. The results suggest that the process of effective conflict resolution is influenced by the context in which it is measured. Different skills drive socially competent adolescent behavior in conflict situations depending on the nature of the interaction, with direct implications for the implementation and evaluation of curricula designed to enhance social skills. Tables and references