This study investigated the relationships between affective and cognitive empathy, social preference and perceived popularity, and involvement in bullying situations by bullying others or defending the victimized children. The participants were 266 primary and 195 secondary school students. Affective and cognitive empathy, as well as the status variables, had some significant main effects on involvement in bullying. In addition, several interaction effects emerged. For instance, the positive association between affective empathy and defending behavior was stronger among boys who had a high status (i.e., were highly preferred) in the group. The results highlight the importance of studying child-by-environment models, which take into account both child characteristics and interpersonal variables in predicting social adjustment.