This article focuses on the dynamics at play in a challenging lesson observed during the LGBTQ unit in a social justice-focused high school course. On the surface, the lesson was a chaotic struggle involving a tense intergenerational clash between the teacher and an outspoken group of students. Young people interrupted and refused the teacher's lesson plan. In response, the teacher raised his voice and consistently tried to redirect the students back to his priorities for the unit. In this article, I am interested in how the teacher and the students were limited in their engagement with each other by the distances imposed by the adult/youth binary that remains so central to schooling. This constraint participated in the failure of this lesson and, most importantly, the failure to communicate across divided understandings of queerness. Drawing on Quinlivan's framework of affective failure, I rethink the possibilities of this lesson, and the teacher/student relationship involved, through the three facets of affective failure: the queer art of failure; affective silences; and engaging otherwise. I seek to explore what relationships, pedagogical and otherwise, could become possible if we reject imposed hierarchies and make space for affective connection in the classroom.