Many students in my undergraduate American politics courses struggle to see policy issues as complex. Too often, they get stuck making surface-level observations or jumping straight to personal opinions, falling far short of critical thinking. This article introduces an active-learning exercise—situational mapping—that provokes students to recognize and think critically about the complexities of policy issues such as immigration, abortion, campaign financing, and guns. Adapted from a grounded-theory research technique, the goals of this mapping exercise are to (1) help students see policy issues as messy, (2) encourage them to “wallow in complexity” rather than oversimplify, and (3) provoke them to think through complexities before forming conclusions. The learning exercise actively engages every student, is simple to prepare and implement, can be completed during a 50-minute class, and is flexible in its application. It also involves teamwork, informal presentations, moving around the classroom, and opportunities for creativity.