The challenge of understanding another person and what it takes to truly feel understood by another is at the hub of human social existence. Psychodramatic role reversal is a related method, rooted in classical role theory, in which two individuals each take the role of the other in an interpersonal situation and actually behave as if one is the other, before returning to their primary selves. In this exercise, every member of the dyad has to overcome both physical constraints and the natural tendency to adhere to one's own viewpoint. This requires empathic abilities as well as creative imagination. Simultaneous holding of two mental representations, one's own and another's, may be a mechanism by which this task could be achieved. Psychological and neurobiological research is presented in favor of this assumption and the concept of creative empathy is introduced as a target for future quantitative and qualitative studies.