Roleplaying games, especially when augmented with the affordances of virtual reality, have the potential to foster prosocial behaviors by facilitating positive perspective taking. In roleplaying games, the orientation phase is particularly crucial, as it provides players with the necessary background information about their role and simulated scenario. However, little research has focused on the effect of orientations in players’ tendency to engage in transformative learning and perspective taking during roleplaying games. To address this gap, we conducted an experiment examining the impact of affinity-specific orientations (information that portrays the role as in- or outgroup) on players’ perceptions in a VR-based roleplaying game called On the Plane. Our qualitative findings indicate that orientations influence players’ appraisal of roleplay characters and their engagement in transformative learning and perspective taking.