A Third Gender: Beautiful Youths in Japanese Prints was an exhibition curated by Asato Ikeda for the Royal Ontario Museum which included many prints and artifacts depicting the wakashu in Edo Japan. The wakashu, male youth who were distinguished from both adult men and women to be represented as “a third gender”, were depicted by the exhibition in conformity with contemporary queer aesthetics and trans identities. This paper explores the curatorial practices involved in the representation of the wakashu as a third gender or gender-queer figure, elucidating the many (re)appropriations involved in the production of a postcolonial queer visual imaginary. I begin by walking through Ikeda’s A Third Gender exhibition, and recounting the representational practices therein, to examine the construction of the wakashu as an essentially gendered figure and exhume the historical and cultural characteristics that are elided by this re-presentation. I then explore the incommensurability of the wakashu with contemporary queer and trans representational practices as a fundamentally queer failure, which may precipitate other affective relations with this figure that transcend our spatial and temporal differences. Finally, I question how these inappropriate/d re-presentations might produce an affective rupture within the queer visual imaginary that invites us to interrogate the postcolonial and transnational structuring of sexuality and gender.