This study tested whether adolescents' attachment style is related to friendship interactions and perceptions of friendship quality. Attachment pairings were contrasted to examine whether dyad members' security of attachment or their models of others was more related to friendship. A total of 44 pairs of same-sex adolescent friends were videotaped as they engaged in an intimate conversation. Participants also completed self-report measures of attachment style and friendship quality. Compared with dyads with at least one insecure partner, dyads with two secure members interacted in ways that promoted a sense of connection with each other. In addition, they did not use as many clarification statements, suggesting a smooth conversational style between the friends. When friend pairs were examined based on positive or negative models of others (i.e., dismissing and fearful vs secure and preoccupied), there were no differences. The findings suggest that security of attachment, rather than type of insecurity, is most related to intimacy in friendship.