Oral historians are regularly faced with interviewees who express distressing emotions while recalling past events. How do we interpret these emotions? What is their historical meaning? This article draws on discussions within the history of emotions and oral history literature to examine these questions. It looks closely at an interview conducted for the Australian Generations Oral History Project and argues that in order to understand the expression of emotion in oral history interviews we need to view not only the process of remembering in a life history interview; we also must view that process through a set of entangled relationships between the time of the event and the time of the telling, and between the intersubjectivities present in the interview itself—that is, the transference and countertransference that occur between interviewee and interviewer.