Prosocial teasing is the positive playful form of relational aggression, and studies have found children engage in playful teasing more often than aggressive teasing. Therefore, understanding the basic characteristics or skills that contribute to the more complex social skill of prosocial teasing is important. The current study focused on the role of empathy in students' perception of their engagement in two different forms of relational behaviors, playful and aggressive. Associations between empathy and engagement in playful and aggressive relational behaviors were investigated with 389 fifth-grade students in the Midwest with the Social Skills Improvement System (SSIS) rating scale and modified Children's Social Behavior Scale--Self-Report (CSBS-S), along with gender interaction in those relationships. Results demonstrated that empathy was significantly and negatively related to the level of engagement in both relational aggression and prosocial teasing. No gender differences were found in levels of relational aggression or in prosocial teasing. Gender differences were observed in empathy, where girls reported higher levels of empathy than boys. Results indicated that empathy was a significant predictor of engagement in both relational aggression and prosocial teasing for both fifth-grade boys and girls. Implications concerning these findings are discussed.