This article addresses the difficulty of engaging middle school students who don't seem to care about learning. Several classroom vignettes illustrate practical, classroom-based dilemmas generated from a university classroom management course. Three positive engagement principles are proposed to address the challenge of the reluctant learner: get to know your students so that they can experience an informed and interested role model; take time to talk to students even as they push you away; and don't take student antagonism and inaction personally by taking a step back, instead build trust and use positive regard. The complicated nature of the reluctant learner requires an array of adaptive, teacher behaviors.