This article examines the kinds of relationships that nonteacher educators, especially youth development practitioners working in after-school settings, have with students. It addresses the fact that these adults in schools have an explicit youth-oriented and relational approach, find out many productive and anxiety-provoking facts about their students, and often do not have sufficient training and supervision to deal with the problems that emerge. It also examines the issue that the roles of these practitioners are varied and differ from the often very defined roles of other school personnel. The article divides the typical functions of the youth development practitioner into three main domains: educator, mentor, and connector. (Contains 1 note.)