In this paper we do two things. Initially, we explore the experience of gender and sexuality non-conformity for boys in school. Here, the designation sissy boy is interpreted through shame dynamics produced in part by the linguistic violence of designation. From this we consider the development of what we call epistemophilic resolutions--the falling in love with knowing that realigns the sissy boy within the school's discursive terrain. As a tentative and unstable resolution to gender and sexuality non-conformity, the epistemophilic resolution operates as a masquerade (after Riviere, 1986). Interpreting this resolution as masquerade allows us, in the second section of this paper, to speculate about the political potential inherent in the anxiety that underpins the operation of epistemophilia as a resolution to the shame of sexuality and gender non-conformity. This offers, in our interpretation, a resistance to (fore) closure and thus a disruption to discursive reproduction. (Contains 1 note.)