This article analyzes student reactions to a course on critical perspectives of social entrepreneurship. Conceptualizing student reactions not merely as resistance but as a breaking up of ‘illusions” that students nurture about their selves make these reactions both more graspable for teachers and possible to influence. First, the article suggests that student reactions need to be acknowledged and comprehended in their complexity, and that teachers adjust pedagogical approaches to students’ abilities and the level of awareness. Second, the article examines processual and relational aspects of critical pedagogy and identifies in student reactions a sense of ambivalence that makes students alternate between resistance/rejection and curiosity/attraction. This ambivalence implies that reconstructive, or hopeful, aspects of entrepreneurship are important in critical curricula in order to complement more deconstructive or skeptical aspects. From a relational point of view, it is desirable that teachers support students in their learning processes by creating a safe and trusting space for learning. The article also discusses the responsibility and sensitivity of teachers and suggests that teachers’ acceptance of own feelings of insufficiency, shame, or vulnerability plays an important role in creating spaces that favor learning and mutual trust between teachers and students.