Changing enrollment profiles have introduced differences in demographics, ability, and interest among the learners in higher education classrooms. As a result, faculty must now accomplish their jobs in a fluid environment with new teaching strategies. Their partners in this work are student affairs staff, who usually educate students in a far less formal capacity: heavily involved in planning the cocurriculum and complementing student academic experiences, this group tends to student needs outside the classroom. In order to provide as effective an education as possible, faculty and student affairs staff must complement each other. History and literature suggest, however, that attaining this relationship is a difficult task that involves considerations of culture, expectations, understanding of student learning, and not-so-simple logistics. This article explores these issues, outlining the challenges of collaboration and the opportunities to make it happen. (Contains 1 figure.)