This study examined how current parent-adolescent relationship qualities and adolescents' representations of relationships with parents were related to friendship interactions in 200 adolescent-close friend dyads. Adolescents and friends were observed discussing problems during a series of structured tasks. Negative interactions with mothers were significantly related to adolescents' greater conflict with friends, poorer focus on tasks, and poorer communication skills. Security of working models (as assessed by interview) was significantly associated with qualities of friendship interactions, whereas security of attachment styles (as assessed by questionnaire) was not. More dismissing (vs. secure) working models were associated with poorer focus on problem discussions and weaker communication skills with friends, even after accounting for gender differences and current parent-adolescent relationship qualities. We discuss possible mechanisms for the observed links between dimensions of parent-adolescent relationships and friendships. We also consider methodological and conceptual differences between working model and style measures of attachment representations.