Background: This chapter explores player interactions and engagement in tabletop role-playing game settings. Objective: Particularly focusing on the intersection of gaming systems, virtual settings, and player interactions, this chapter seeks to explore how implicit systems shape individuals' experiences and behaviors. Through this focus, the chapter intentionally draws parallels between informal gaming settings and classroom-based interactions. Setting: Though this study makes specific connections to classroom pedagogies, data were collected from a multiyear ethnographic study of playing tabletop role-playing games with adult participants in informal learning environments. Data were collected from within public gaming cafes and shops. Research Design: Participant observation within a role-playing game community served as the primary approach to this ethnographic study. In addition to fieldnote-based observation, interviews with players and archival analysis of gaming artifacts helped triangulate meaning-making at the gaming table. Analysis was conducted through an inductive coding approach that focused on player interactions, systems, and settings. Findings: Cultural values, including racism and sexism, shaped player experiences at the table, based on systemic designs and textual guidance from game-related fiction. While games speak to broad possibilities for exploring race and gender, these constructs become limited through the layers of player beliefs, designed rule sets, and depictions within narratives. The emancipatory possibilities of ludic imagination are flattened by cultural norms that may oppress. Conclusions: Broadening the findings from this study, this chapter concludes with classroom-based recommendations. If a contemporary approach to critical pedagogy depends on dialogue and cultural understanding, this chapter points to the limitations of confining such work to traditional classroom settings. Instead, it suggests that an interrogation of these systems, alongside youth, is a necessary step in critically oriented classrooms.