Acclaimed as the central science, the borders of chemistry join those of many other human interests and concerns with their associated academic disciplines. Mentoring undergraduates in research that straddles or crosses those borders can be challenging and risky, but also rewarding and beneficial to students and mentor alike. Varieties may be characterized by distance from the border. The practice of chemistry as “the molecular science” may be juxtaposed to other disciplines in a coordinated investigation (perhaps in an area not normally associated with chemistry) where insights result from the disciplines interacting in a synergic manner. One professional example is Joseph Nagyvary's research on Stradivarius violins. In another variety, a related discipline may be applied to chemical problems (for example, in statistical analysis of chemical data). Such research will still be recognized as “chemistry.” More radical excursions make use of the chemist's skills and approaches beyond the borders of the discipline. Examples will be given, including undergraduate research in science and religion, science and ethics, public health policy, and mathematical epidemiology. Some factors that may affect the feasibility or advisability of such research will be discussed.