School-based supports, such as LGBTQ+ -themed curriculum, invite opportunities for challenging oppression with respect to gender and its intersections with other identities such as sexuality and race. However, more understanding is needed regarding how literacy educators might leverage these opportunities. This article describes how intimacy, oppressive actions, and activism functioned in relation to one another in an LGBTQ+ -themed literature course at a grassroots public charter high school for the arts in a mid-sized Midwestern city. The larger study, from which this article is derived, is a hybrid of ethnography and practitioner inquiry. Therefore, this study draws on field notes, transcribed video recordings of class, transcribed audio recordings of interviews, and student assignments related to a young adult novel. Our analysis of gendered power relations suggests that oppression can hinder intimacy, intimacy can hinder activism, but intimacy can also foster activism. With the goal of leveraging opportunities to challenge gendered oppression, we argue that students and teachers must navigate intimacy and intersecting structures of oppression to enact activism.