When assessing North American students' oral participation in classes, should all students be subject to the same evaluation criteria or should teachers make reasonable allowances for Asian students practicing humility? How do we weigh the promotion of "courage" through character education initiatives with traditional Asian dispositions? Viewing Asian humility in Western classrooms and as it rubs up against liberal principles of equality or justice, and a virtue ethic raises a number of philosophical questions around authenticity, polyvalence, and relativity. I approach first through the lens of liberal philosophy as the "dilemma of diversity" meets a boundary with communitarianism, and then through the contextualist lenses of Wittgenstein, Heidegger, and Foucault. Drawing on Tully's political philosophy, I inspect humility as embedded in language-games and then open it to revision through comparative history, inviting participants in the teacher's game of assessment to renegotiate the rules: a process complicated by their reticence to speak up. I also use Medina and Scheman's political reading of Wittgenstein to discuss how teachers can discern humility as "performative" silence within the classroom, distinguishing between genealogical accounts that show how comportments could be otherwise from perspicuous inspection of interconnected language-games in current educational settings. (Contains 8 notes.)