This paper considers affective interactions to achieve empathic engagement with synthetic characters in virtual learning environments, in order to support and induce the expression of empathy in children. The paper presents FearNot!, a school based virtual learning environment, populated by synthetic characters used for personal, social and health education, specifically bullying issues in schools. An empirical study of 345 children aged 8-11 years who interacted with FearNot! is outlined. The results identify that affective interactions resulting in the expression of empathy were increased when children had high levels of belief and interest in character conversations and if they believed that their interactions had an impact on the characters' behaviour. © Springer-Verlag Berlin Heidelberg 2005.