Growing up in Greenpoint, Brooklyn, I spent much of my youth in the public library finding books to read so I could entertain myself when accompanying my mother while she cleaned apartments. It was at the library that I first encountered the Classics, reading Suetonius far earlier perhaps than I should have. Since that time, I have had a great fascination with Greek and Roman antiquity and with the representation and history of sexuality in particular. More recently, I developed increasing interest in transgender studies and have found that Classical texts provide important reflection on current debates on gender. Not only is this material close to me as a scholar, but I believe that its careful study will also act as an invitation for the transgender community to push beyond the boundaries of established scholarship. As such, my scholarly interests and social action join a larger movement to rethink the paradigms and limits of gender and sexuality. I hope to show the utility of not only the Classics, but the Humanities as a whole, to act as a valuable analytical and intellectual toolkit that students can use to grapple with the sometimes painful questions of identity that resonate with them.