This essay relies on methods of narrative research to both present and consider an example of a second-wave of critical whiteness pedagogy in K-12 contexts. The author focuses on his interactions with one high school student -- Adam -- to theorize how "The Whiteness Project" allowed students to "play with whiteness" in generative, disruptive, and often confounding ways that are not afforded by traditional anti-racism pedagogies with white students. This essay considers a potential move toward playfulness, openness, and radical engagement in anti-racist whiteness pedagogies in schools.