Research finds that males are more likely to engage in delinquency than females. General strain theory (GST) suggests that males and females experience different emotions in response to strain leading to different deviant outcomes. Tests of GST to account for this issue are mixed, perhaps due to the reliance on measures that fail to take into account the gendered nature of responses to strain. The current study examines the mediation of strain by negative affect in the pathway to deviance using both a measure of externalizing deviance more commonly found among males (fighting) and a measure of internalizing deviance that is more commonly found among females (cutting oneself). Results indicate that emotions mediate some of the impact of strain on deviance and, while the path from strain to emotions is similar for boys and girls, emotions have differential effects on externalized and internalized deviance depending on sex.