In "Teaching to Transgress," bell hooks is both welcoming and suspicious of those who would teach from a position that recognizes the limitations of personal experience. Teaching from experience can lead to a difficult and defensive essentialism that relegates students and teachers alike to categories and "types," and, as hooks argues, can obscure real cultural understanding of privilege and oppression, neither of which respects clear-cut boundaries of skin color or gender. As a straight white man, an Anglo professor of French, and the only male at his university to teach WGST 106: Introduction to Women's Studies, the author is acutely aware of the paradox hooks highlights for those who teach what they haven't experienced. In this essay, he underscores the challenges hooks's paradox presented during his first semester in WGST 106, a semester that necessitated an intricate pedagogical balancing act on his part as he attempted, from a position of masculine privilege, to teach female students to reject "conventional oppressive hierarchies." This essay is about pedagogy rather than biology. Indeed, it addresses what critics like hooks might consider pedagogically precarious, that is, the author's attempt as a man to introduce college-aged women to feminism. (Contains 8 notes.)