In the fall of 2021, an engaged group of NYU graduate students assembled to discuss Angie Thomas' YA novel "The Hate U Give." The class was composed of one Black student among a group of white students. On the night the group discussed "The Hate U Give," the freedom of discourse broke down significantly. The white students became terrified of saying anything that could be perceived as racist, while the Black student felt resentful that she should be expected to 'teach' the rest of the group about being Black in America. In this article, the white professor and the single Black student in the class reflect on what factors disrupted the group from having a meaningful conversation about race. The piece aims to help both Black and white students and educators more successfully navigate difficult conversations centred around race.