We developed, implemented, and evaluated a participatory arts-based storytelling initiative called the Reflection Room project. Our aim was to investigate if visiting a Reflection Room, (1) creates opportunities for disclosing emotions and processing thoughts, (2) increases comfort discussing dying and death, and (3) supports advance care planning (ACP), conversations. In the pilot phase of the Reflection Room project, a Reflection Room was installed in 25 sites across Canada from 2016–2017. Data collection included reflection cards ( n = 463), and surveys completed by visitors upon exiting a room ( n = 271) and 3 months later ( n = 50). Analysis involved theoretically driven coding, inductive content analysis, and descriptive statistics. We found reflections contained both emotional disclosures and reflective processing. Survey data indicated visiting a Reflection Room increased comfort in thinking and talking about dying and death as well as the likelihood of engaging in ACP. In the future, we will explore the extent to which the project fosters social connections and well-being.