I made a recent realization: discussing complex gender issues leaves me speechless. I realized that after about the 14th time I tried and failed to begin this article. This new manifestation of my ignorance comes courtesy of the MIT List Visual Arts Center’s exhibition entitled Virtuoso Illusion: Cross-Dressing and the New Media Avant-Garde. The exhibit covered themes of alternative identity, gender roles, and sexuality. I was strongly drawn to two pieces in particular, one of which was Michelle Handelman’s video “Dorian” (2009), the other was Kalup Linzy’s “Conversations wit de Churen III: Da Young & Da Mess” (2005).