This dissertation consists of three articles united by the question: what happens when we engage with the lives of people of the past? In recent decades, history educators in a number of learning environments have increasingly replaced impersonal, monolithic historical narratives with accounts of real people and their lived experience. These efforts have been part of broader attempts to make history learning environments less focused on the memorization of names and dates, and more focused on "doing history" in the ways that historians do: carefully using historical evidence to understand the contexts within which past people lived. While a great deal of rigorous research has been conducted on historical thinking, we know very little about what happens in moments of one-on-one engagement between a present-day person and a past person. The traces of the real people of the past spark many kinds of thoughts and feelings in modern-day people, yet researchers have rarely considered the psychology of these moments of past/present connection. Instead, they have used vague metaphors in saying that past people "bring the past to life" or "put a face to history." What are the psychological nuances behind these metaphors? Each article is based on a study that approached the overarching question in a different way. Article I focuses on the act of historical perspective taking, creating a framework for understanding how people think as they explore the perspective of past people. Article II confronts the question of how to overcome the barriers that make it difficult for present-day people to understand the perspective of past people perceived as evil--specifically, Holocaust perpetrators. It tests whether a brief exercise in which one is guided to think and write about one's values facilitates one's subsequent engagement with Holocaust-related material. Article III examines the experiences of visitors to a museum exhibit that is replete of images and accounts of past people, and it presents a framework for analyzing how visitors connect with and learn from these representations of past individuals. Altogether, the dissertation illustrates the diversity of questions that stem from thinking more deeply about past/present interpersonal engagements. It raises this as a topic unto itself among other aspects of historical thinking such as evaluating a historical source, corroborating it with others, and placing it into context: how do the kinds of engagements investigated in this dissertation tie into such processes? It also demonstrates that theory and methodologies used by psychologists have much to offer history education research. Finally, the dissertation comes together in that it proposes a set of tools intended to help history educators understand their learners better and to help researchers deepen their analyses of this crucial aspect of historical thinking. The following are the abstracts of the individual articles. Abstract of Article I: This article presents a framework for understanding historical perspective taking (HPT), the effort to use historical material to explore and reconstruct the internal states of past people. It addresses gaps in HPT research by (a) linking HPT to theories and research from the social science disciplines on perspective taking and the self, and (b) proposing a way to analyze how different tasks may elicit different kinds of HPT. The framework is grounded in a study where four young adults thought aloud while taking the perspective of a victim or a perpetrator at the Salem Witch Trials and a Holocaust-era massacre. Four "self perspectives" were identified, whereby participants thought as their present-day selves, constructed hypothetical and imagined past selves, and made timeless generalizations about humans. All participants shifted frequently among these perspectives, suggesting a variety of learning processes. To demonstrate the utility of the framework, it is then used to consider how task characteristics--such as taking the perspective of a Holocaust perpetrator vs. a person accused of witchcraft--may have elicited differential use of the self perspectives. It is argued that close attention to these self perspectives is a crucial and novel way to bring nuance to the concept of HPT, and implications for multiple learning environments are discussed. Abstract of Article II: When trying to understand people who are different from us, it can be all too easy to dismiss them as strange or as inherently evil. This may especially be true with regard to Holocaust perpetrators, where attempting to take their perspective may threaten the self as one questions, "What if I had been one of them?" This article explores data from two experiments that tested a means of reducing this threat: a values affirmation, where one is guided to think and write about one's values. Participants completed a web-based survey in which they were randomly assigned to complete a values affirmation or a control task. They were then asked to read an article about how psychologists can help us understand the complex social dynamics of the Holocaust-era massacre at Józefów, Poland. Participants answered questions that gauged their openness to understanding the perpetrators' perspective, their comfort level, and their empathy. They were asked similar questions about a second article, on the perpetrator of terror attacks in Norway in 2011. It was hypothesized that those who completed the affirmation would show more openness, comfort, and empathy than control participants. Most results were contrary to the hypotheses, however. The data are explored for explanations and patterns that may be instructive for further study, for instance, the effect that writing about the value of "relationships with family and friends" may have on confronting the subsequent historical material. Implications for learners in a range of environments that use challenging historical material are discussed. Abstract of Article III: Article III explores how museum visitors engaged with representations of real people of the past (RRPPs). While educators have widely argued that RRPPs "bring history to life" and benefit learners in various ways, there has yet to be a systematic consideration of what visitors actually do with the representations of the real people they encounter. This article is based on a qualitative study of how 12 museum visitors engaged with RRPPs they encountered in an exhibit, on the California Gold Rush, that foregrounds RRPPs and minimizes curatorial interpretation. Participants "thought aloud" while visiting the exhibit, wearing a GoPro camera mounted to their foreheads to capture their voiced thoughts and what they were seeing and doing, and they were interviewed after their visit. From the coded transcripts, a framework is constructed to account for how participants used RRPPs both as means of interpersonal connection, and as sources for gathering information. Within this framework, six distinct kinds of connection are elaborated. The framework is used to characterize different ways in which participants engaged with the RRPPs--the degree to which they connected and/or gathered information--and in-depth portraits of four participants who showed different patterns of engagement are provided. Questions and concerns are raised about potential benefits and drawbacks to the use of RRPPs in exhibits such as this, and implications for a range of learning environments are discussed.