Four professors discuss the complexity and challenges of teaching the psychology of men. The authors present different assumptions and contexts for their course. Each professor describes developmental process of helping students deconstruct gender roles and personalize the psychology of men using an array of classroom practices ranging from traditional pedagogy to psychoeducation. They discuss issues related to critical thinking and how to deal with resistance and defensiveness. Managing classroom dynamics and addressing multiple oppressions are addressed as challenging but fundamental to the teaching of the psychology of men. The authors also discuss how a psychology of men course affects students and how they manage the complexity of interactive classrooms. A common theme across courses is the excitement that emanates from teaching the psychology of men, with many students reporting significant personal development occurring as they deconstruct gender roles and apply the learning to themselves and their professional lives. All the professors report that teaching the psychology of men is challenging, provocative, and enjoyable.