This paper considers the positionality of a Man of Colour studying Whiteness among male undergraduates, and the methodological challenges this poses. While some have explored the politics of representation when a researcher comes from the socially dominant group or from the same racial group there are almost no explorations of the researcher/participant dynamic when the scholar comes from the socially marginalised background. This article chronicles one researcher's methodological approach to this issue. In particular, it explores the way that interviews can become sites of racial microaggressions against a Scholar of Colour, and how a researcher insufficient taking account of his unconscious masculinity almost derailed the critical interrogation of Whiteness.