Ann Hirsch is an emerging video and performance artist based in Brooklyn, New York whose work focuses on women’s sexuality on the Internet. Hirsch’s digital work is constantly in flux, appearing, disappearing and reappearing online. Her work, like her identity, reflects the possibilities of self- representation at the turn of the millennium. The paper that follows examines Hirsch’s artwork Twelve (2013) and its evolution from a pseudo biographical eBook to an art object, a shift which transpired during the course of my own research and engagement. A complex piece addressing the nexus of youth culture, online intimacies and social regulation; the transformation of Twelve’s construction and preservation indicates the possibility for a teleological shift in new media scholarship that recognizes the ephemeral nature of technology- dependent art and the slower pace of traditional forms of academic scholarship. The speed of production, destruction, and reconstruction of Twelve is distinct to new media art fields and digital cultures.