The purpose of this study was to measure children’s estimations of social pain using a virtual reality (VR) bullying simulation. A mixed methods design was employed, measuring social pain scores, empathy gaps, gender differences, and exploring children’s explanations for victimization. A child sample (n = 142) completed imagine-self perspective-taking tasks before and after they virtually experienced the perspective of a victim or a bystander. VR perspective-taking did not increase social pain scores and no evidence of the empathy gap was found. Gender differences were found in social pain appraisals, with females estimating higher scores. Responses to an open-ended question suggested that children explain victimization through individualistic reasoning.