Many art educators and critical media educators that strive to teach and raise students’ critical consciousness about media have encountered a dilemma: whether or not it is possible to solicit criticality among students through pedagogical exchanges given the power dynamics inherent in “teaching.” Following other art and critical media literacy educators’ experimental approaches of designing curriculum that explicitly integrated themes of gender, I developed an action research study of an afterschool program focusing on critiquing and producing video game related media along these themes, which spun the course of five weeks with youth in a library setting. Through this study, I argued that the dilemma in teaching criticality is the outcome of confusing teaching critical discourse, understood here as arguments and critiques informed by critical theories with teaching criticality, understood here as exercising one’s reflexivity in generating critiques. I demonstrated my reflections on this dilemma by considering criticality developmentally in terms of a modified version of Kohlberg’s moral development theory (1984). Criticality is complex in the sense that it manifests differently for actors in various positioning. In return, there was no critical discourse that could represent the critical consciousness of everyone and teaching criticality requires pedagogues to emphasize on recognizing students’ moral developmental differences about critical discourse.