Virtual Reality (VR) has been increasingly referred to as the "ultimate empathy machine" since it allows users to experience any situation from any point of view. However, empirical evidence supporting the claim that VR is a more effective method of eliciting empathy than traditional perspective-taking is limited. Two experiments were conducted in order to compare the short and long-term effects of a traditional perspective-taking task and a VR perspective-taking task (Study 1), and to explore the role of technological immersion when it comes to different types of mediated perspective-taking tasks (Study 2). Results of Study 1 show that over the course of eight weeks participants in both conditions reported feeling empathetic and connected to the homeless at similar rates, however, participants who became homeless in VR had more positive, longer-lasting attitudes toward the homeless and signed a petition supporting the homeless at a significantly higher rate than participants who performed a traditional perspective-taking task. Study 2 compared three different types of perspective-taking tasks with different levels of immersion (traditional vs. desktop computer vs. VR) and a control condition (where participants received fact-driven information about the homeless). Results show that participants who performed any type of perspective-taking task reported feeling more empathetic and connected to the homeless than the participants who only received information. Replicating the results from Study 1, there was no difference in self-report measures for any of the perspective-taking conditions, however, a significantly higher number of participants in the VR condition signed a petition supporting affordable housing for the homeless compared to the traditional and less immersive conditions. We discuss the theoretical and practical implications of these findings.