This study examines the close friendships of early adolescent boys in relation to antisocial behavior. 186 13-14-year-old boys and their close friends were interviewed, assessed at school, and videotaped in a problem-solving task. Similarity was observed between the demographic characteristics and antisocial behavior of the boys and their close friends. There was a tendency for the close friends of antisocial boys to live within the same neighborhood block and to have met in unstructured, unsupervised activities. Direct observations of interactions with close friends revealed a reliable correlation between antisocial behavior, directives, and negative reciprocity. Positive interactions within the friendship were uncorrelated with antisocial behavior and relationship quality. Implications of these findings for clinical and developmental theory are discussed.