On the basis of analysis of student responses to a case study titled "Drinks and Dinner," the authors evaluate the pedagogical potential of using constructive controversy case studies to teach about inequality. "Drinks and Dinner" is designed to capture the complexity of social interactions that defy simple solutions to engage students in increasingly sophisticated discussions of subtle gender bias and the practical contingencies of power in the workplace. Having taught the case several times in two distinct institutional cultures, the authors use student reactions to this classroom exercise to consider some of the pedagogical payoffs of constructive controversy case studies. The intentional ambiguities written into "Drinks and Dinner" defy simple solutions and require students to discuss while incorporating, honoring, and addressing differences of opinion, not only among the characters in the story but also among the students in the classroom. In the authors' preliminary implementations of the case, they found that students applied course concepts, considered multiple viewpoints, and, in some cases, moved from individualized explanations to structural analysis of how inequality is reproduced. The authors conclude with ideas for how to implement similar cases in other courses that could benefit from requiring students to actively and collectively solve problems related to inequality and the routine use of power. (Contains 5 notes.)