This article describes activities that can be used with multiple audiences of teachers, administrators, or other caregivers regarding setting boundaries in personal relationships with students. First, participants must think about and discuss relationships that they experienced with their own teachers in the past and determine what aspects of those relationships made an impression on them. In many cases, these connections deeply influenced teachers to join the profession. Second, participants consider dilemmas that they would realistically face with students and decide how they would respond. The dilemmas are derived from actual encounters teachers describe in this volume and elsewhere. In groups, they discuss what the ramifications might be in each circumstance and explore together sound and appropriate responses. Finally, there is an emphasis on the process of strategizing well before these dilemmas arise.