In this article, two art teacher trainers explore the possibility of saddling critical pedagogy with queer theory in order to question the art curriculum's potential for critiquing personal relationships. As a preadolescent boy, one author initiated his own sex education curriculum with his middle school peers by creating "secret nude sketches" in order to prompt conversations about sex and sexuality. The other author considers his efforts to challenge the conventions of assessment and personal reflection by radically combining these activities into an alternative mid-term examination. By paralleling their teaching and learning experiences, the authors begin to grapple with multiple aspects of their identities within and outside of the curriculum. This article suggests that approaching curriculum as a set of actions built toward conversations of understanding will help art teachers queer spaces between themselves, the classroom, the students, and the world.