In this paper, I explore empathic understanding vis-à-vis the television series Star Trek: The Next Generation. I present scenes from an episode of The Next Generation as case studies and analyze them to reveal the external and internal nature of language, as well as the “delusion” of a shared language. I also use these scenes to highlight the difference between understanding and empathic understanding, errors in empathic understanding found in the Wisconsin Project, and the usefulness of pre-therapy in expanding therapist awareness and appreciation of empathic understanding. I also delve into the roles played by psychological contact, congruence, and unconditional positive regard in supporting empathic understanding, as illustrated by the pop-culture vignettes I provide.