A growing literature highlights the benefits of playing the classic board game Diplomacy in international relations (IR) courses. But how exactly can it help students to learn not only about different IR theories, but also about what it means to "use" a theory in the first place? To address this question, I highlight my experiences overseeing the game during the first 2 weeks of seven introductory IR classes. Drawing from debriefing worksheets that 151 students completed after playing it, I examine whether they (1) made (implicit) connections to various theoretical perspectives and (2) developed a critical appreciation of theoretical abstraction and simplification. I find that the game's social and collaborative components lend themselves to theories beyond neorealism. More importantly, I show that by modeling rather than replicating world politics, Diplomacy introduces students to a counterintuitive idea: that theories can reveal things about reality even as they distort and omit parts of it. Moreover, having students reflect on the game's limitations encourages them to fill in the gaps, anticipate topics covered throughout the semester, and recognize the challenges of putting theories into practice.