Depression, anxiety, and suicidal thoughts or actions are on the rise in adolescents (National Institute of Mental Health, 2015; Bridge, Asti, & Horowitz, 2015). Parents, school administrators, and therapists are searching for resiliency factors with in at-risk groups to aid students in need. In previous work, Luthar and Zigler (1992) reported that intelligent youth are more resilient than less intelligent youth under low stress conditions but they lose their advantage under high stress conditions. This study examined whether intelligence (reflected in grade point average; GPA) and maladaptive (internalizing and externalizing symptoms) behaviors are negatively related in adolescents, and tested whether level of stress, reflected in emotion regulation and friendship quality, moderated that association. It also probed whether the relationships differ by gender. Sixth-graders (N=506) were recruited with active parental consent from three middle schools. Adolescents completed self-report questionnaires Regarding demo graphics, maladaptive behaviors, emotion regulation, and friendship quality, and GPA data were collected from the school. Regression analyses found that GPA was negatively related to externalizing symptoms. Girls with poor friendship communication report significantly higher maladaptive behaviors. This relation was more pronounced for girls with high GPAs, as predicted. Results support the theory that intelligent female adolescents are more reactive under adverse circumstances. Future efforts should follow students through middle school into high school to evaluate whether friendships remain important to adjustment, hold for boys as well as girls, and have implications for relationship interventions.