In this paper, I describe an innovative assignment for teaching undergraduate students cross-cultural understanding. The Outsider/Insider assignment simultaneously teaches facts about cultural difference and skills for managing cross-cultural encounters. Briefly, the assignment is to write two short papers, one in which the student describes a situation in which he or she was the outsider, and the other a situation in which he or she observed a newcomer to a group where that person was an insider. The paper begins by reviewing previous research on cross-cultural interaction and its relevance for pedagogy, and describing the course, its goals, and the "Outsider/Insider" assignment. The effectiveness of the assignment is demonstrated through an analysis of excerpts from student papers. This analysis shows how the assignment can accomplish learning on a range of dimensions. The main themes that will be addressed are the following: (a) being seen as the outsider; (b) challenges related to outsider status; (c), the relevance of social class, poverty, and wealth on insider/outsider status; (d) strategies for coping in cross-cultural encounters; and (e) benefits to the student of being willing to cross boundaries. The paper concludes with a discussion of how the assignment facilitates student learning and its relevance for a range of undergraduate courses.