SummaryResearch is increasingly demonstrating that authenticity and human connection are fundamental and interrelated human needs. However, organizational roles often constrain authenticity and connection in workplace interactions, especially roles that are highly scripted. People want to feel authentic and connected at work, but they also need to adhere to role expectations. Organizational role scholars have long explored how roles cause feelings of inauthenticity, and more recently, the conditions that promote authenticity. We have limited understanding of how people approach being authentic in their roles without compromising or deviating from rigid role demands. To explore this, I conducted an inductive, qualitative study of six community theater productions, a context where roles are rigidly scripted, yet where actors strive to “live truthfully” within their fictional roles. I find that actors and directors work together to cultivate authentic interrelating in their roles, characterized by the combination of personal engagement and interpersonal attunement. This process involves engaging in different forms of play to move from mechanically learning their roles, to crafting personalized intentions, to ultimately transcending their roles, gradually increasing in vulnerability and responsiveness until they are able to experience authentic interrelating in their roles.