Diaries can serve as meaningful entry points for advancing historical consciousness and develop historical thinking (Seixas, 2002) because they can connect readers/learners with the diverse emotions, thoughts and motivations of the people who wrote them in particular times and particular places. According to philosopher and historian, R.G. Collingwood (1994/1946), historical thinking and meaning-making involves exploration of both the "outside" (that which would have been observable: "bodies and their movements") and the "inside" (that which would have been unobservable: thoughts, emotions, motivations) of past human actions. One of the tasks and tensions of historical work is to get to the "inside"--to bring out (reveal or reconstruct) and contextualize ways of thinking and feeling represented in documents and artifacts left behind, so that one can understand both the similarities and differences in how people viewed the world. In this paper, the author will: (1) briefly discuss the importance of historical perspective-taking as an aspect of historical thinking and the obligation of educators to assist learners in developing their capacity to engage; (2) outline why and how teachers could assist learners in using diaries as evidence for reconstructing historical perspectives; (3) layout excerpts from three published diaries to demonstrate how these provide evidence of classed, gendered, ethnic/religious points of view within the time periods they were written; and (4) provide some specific suggestions as to how teachers can use examples from these diaries to spark deeper probing of ideas and time periods. (Contains 1 note.)