Should we discuss practices around sex and sexuality in early modern Japan as a distinct, foreign phenomenon entirely unique to the period and culture, or can we somehow draw a genealogy and create a trans-historical narrative that ends with today's LGBTQ+ culture? These questions were central to the process of organizing the exhibition A Third Gender: Beautiful Youths in Japanese Prints at the Royal Ontario Museum (ROM) in Toronto in 2016. The exhibition focused on visual representations of male youths, called wakashu in Japanese, who were the object of sexual desire for both women and adult men in Edo-era Japan. Presented in the form of an exhibition, the project necessitated engaging the past with the present and the general public with scholarship. In this short reflection essay, the author and curator explains how the Third Gender project approached the question of Edo-era Japan's trans-historicity.