Understanding ethical boundaries in student affairs work can be challenging and difficult to navigate for student affairs professionals. The purpose of this article is to examine the complexities of dual relationships and the ethical issues that may arise. As a result, the authors offer tools to (a) identify various perspectives in resolving ethical problems and (b) examine the issues using a theoretical model. The article includes a case study embedded throughout the article, a brief overview of ethics in the profession, and tools for ethical analysis that will assist supervising practitioners, graduate faculty, and graduate students under their supervision.