This paper draws on findings from a two-year study of gender and gender transgression among school children and youth in rural Ontario, Canada conducted while running gender equity workshops for students aged 8-18 years, in which I asked participants to document what gender looked and felt like. Through writing prompts, pictures, discussion and theatre, roughly 600 participants had the opportunity to describe gender as well as responses to perceived transgressions of gender. In the course of this work, I became especially interested in the emotions identified by participants as being part of, or experienced through, their gender. In this paper, I focus on notions of happiness, enjoyment and fun, as described by participants in their responses. Happiness is a part of gender that is often overlooked in human rights definitions of gender identity and expression, as well as in the translation of legal discourse into a social justice-oriented curriculum. While participants in this study expressed a wide range of emotions, a focus on happiness offers insights into contemporary definitions of gender, as well as a potentially transformational curriculum for gender diversity.