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Adolescents' friendship quality and observed emotional expression with their best friends were predicted from reports of their mother's interpersonal relationships—specifically the quality of her marriage and social network. Two models explaining these relationships received support. Consistent with an Attachment Theory model, adolescents' perceptions of marital quality predicted attachment security with mother, father and friends. Security of attachment to friends in turn predicted best friendship quality, but not affective behavior with the friend. A Social Learning Theory model was also supported, in which perceptions of both marital quality and mother's social network quality predicted adolescents' prosocial behavior. Prosocial behavior in turn predicted both best friendship quality and affective behavior with the friend.