The best friendships of emotionally distressed and typical young adolescents were investigated. A group of 5th and 6th grade young adolescents completed ratings on friendship quality and participated in videotaped friendship tasks. Emotional distress was identified using a T score cut-point of 60 on the Internalizing symptoms subscale of the Child Behavior Checklist (CBCL). There were 131 friendship dyads available for analyses. Of these, 48 were considered distressed dyads (24 female dyads; 24 male dyads) and 83 were considered typical dyads (47 female dyads; 36 male dyads). Results demonstrated similarity of internalizing symptoms between best friends of typical adolescents, but not distressed adolescents. Analyses on friendship quality ratings emphasized the importance of perspective. Distressed targets rated their friendships lower on validation/caring, help/guidance and total positive friendship quality than did typical targets. However, friends of distressed adolescents did not rate their friendships differently than friends of typical adolescents. Congruent with past research, females tended to rate their friendships higher on intimate disclosure than did males. No developmental differences emerged in analyses of friendship quality. Regarding observed disclosure, only half of the dyads engaged in spontaneous disclosure talk. The majority of disclosures involved negative speech about the self or dyad. Females tended to devote more time to disclosure talk and respond to disclosure in more positive ways than males. Fifth-graders tended to devote more time to disclosure talk, initiate more disclosures and respond in more negative ways than 6th graders. Differences between distressed and typical dyads did not emerge in analyses of observed disclosure. Finally, relations between reported friendship quality and observed disclosure were explored. Overall, a lack of relation among variables suggests that the ways in which adolescents think about friendship quality are not related to visible interactions that took place in the laboratory.