In this study, the relationships among gender, empathetic responsiveness, perceived group norms, prosocial affiliations, and bullying roles were examined for 262 fifth- through eighth-grade students (n = 141 males; n = 121 females). According to the Bullying Participant Roles Survey (BPRS), participants were identified as defenders (n = 135; 51.5%), victims (n = 48; 18.3%), bullies (n = 39; 14.9%), and outsiders (n = 26; 9.9%). Results of multinominal logistic regression revealed that empathetic responsiveness was a significant predictor of defending behavior and an inverse predictor of outsider behavior. Gender also predicted defending behavior, with boys being more likely to defend than girls. In addition, participants who indicated that their friends supported bullying were more likely to be involved in bullying perpetration and victimization. An unexpected interaction effect between prosocial affiliations and group norms indicated that girls who reported more probullying group norms but whose friends reported having more prosocial tendencies were more likely to assume roles of bullies and victims than outsiders. Implications for practice are outlined, including recommendations for antibullying initiatives.