This chapter explores the use of the term “empathy” in UK schools and stresses it is not the definition of “empathy” that is problematic. Rather, “empathy” stands for a certain kind of historical understanding that attempts to clarify what is involved in understanding actions and institutions in the past. To examine debates surrounding the use of “empathy” in the classroom, the authors conduct an overview of theories and literature on the topic of “empathy” and examine students’ epithetical understandings of history in the second and eighth grades through tasks and questions about Roman Law. Students were also asked about the Anglo-Saxon institution of trial by oath helping and the ordeal, and were asked why Anglo-Saxons used the ordeal to determine if someone was guilty of a crime. The research found that there were major differences between the responses of younger and older students. These changes were rooted in an emerging set of “Default” assumptions that students employed to make sense of an historical world that did not necessarily conform to their expectations. These included assumptions about rational action understood in terms of shared human conventions or basic ways humans deal with everyday life; technological progress; increasing knowledge and understanding; rational change; and “event changes” or a belief that change is connected to events. The authors stress that history education is not only about the accumulation of knowledge, but about the development and acquisition of historical understandings.