This paper draws from social science literature on Whiteness and anti-racism as well as personal classroom experience to examine the obstacles educators face in teaching anti-racism to White college students. Emphasis is placed on popular perceptions and common definitions of the word "racism" as it is used in mainstream American society. The authors explore the problems that arise when trying to define anti-racism accurately. Whiteness is critically discussed and analyzed as a cultural myth and as a seemingly insurmountable obstacle to White Americans' adoption of an anti-racist philosophy and practice. Ultimately, the authors stress the importance of reflexivity in the classroom, both for students and teachers, and of dialogue as a tool to create counter-hegemonic narratives. This dialogue is intended to make systems of privilege and oppression visible, specifically focusing on how students may effectively challenge covert racism in their daily interactions.