Students' relationships with authority and information are changing rapidly, and this presents a new set of interpersonal boundary challenges for faculty. The topic of setting boundaries often conjures up thoughts of how to protect oneself. The intent of this chapter is to explore how good rapport between teacher and student can be developed and in turn create an engaging learning environment that promotes self-giving rather than self-protecting behaviors. Connecting with students does not have to be at the expense of academic rigor. Rigor and relationship are not antithetical. This chapter explores generational differences and the Millennial generation in particular and then provides strategies for clarifying, maintaining, and at times adjusting boundaries with Millennial students. Understanding these differences will help faculty members set interpersonal boundaries that create an environment in which both student and teacher feel respected, appreciated, and capable. (Contains 1 table.)