Girls’ maladaptive responses to strain may be more likely to manifest in self-directed deviance than externally directed deviance, partly due to the role of depression/anxiety in girls’ lives. These assertions are tested using the Project on Human Development in Chicago Neighborhoods. Gendered maladaptive outcomes—aggressive delinquency, running away, substance use, and suicidal behavior—are regressed on negative emotions and serious strain. The moderating effects of depression/anxiety are also tested. Depression/anxiety is associated with less aggressive delinquency for girls and amplifies the effects of strain and anger on nonaggressive maladaptive outcomes. The results help explain how gender influences relationships among strain, externalizing and internalizing negative emotions, and risk behaviors.