In this essay Sandra Vanderbilt explores philosophies of peace and protest through a dialectical reading of the works of Martin Luther King Jr., Daisaku Ikeda, and Paulo Freire, and considers these philosophies in relation to her own activism, specifically in the context of dealing with White postracial myths and more overt acts of racism. This essay outlines what she learned from her dialectical reading across several works by King, Ikeda, and Freire, and how these philosophies of peace and protest informed the ways in which she has been able to initiate and sustain conversations across the chasm that separates her antiracist positioning from the stance of friends and family members who deny and enact racism and White supremacy. The three theorists Vanderbilt focuses on here all point to ongoing engagement among individuals as necessary to sustaining the collective. Drawing on their work, Vanderbilt suggests that we have to begin with a critical understanding of Whiteness in our efforts to engage someone, in radically loving acts, in confrontation with their own words and behavior. Opportunities for this sort of confrontation have the potential to bridge the conversational chasm and to open discussions wherein one can practice the virtue of justice, and importantly racial justice.