Race is sewn into the very fabric of advertising, yet it remains largely absent from the practice of advertising pedagogy and from scholarship on teaching advertising. Indeed, most students begin their professional career without earnestly considering the significance of race, particularly their own, in relation to how advertising is coordinated, implemented, and received. As consumer markets continue to become more racially diverse, the relationship between race and advertising is sure to evolve—increasing in complexity and nuance. In order for the next generation of advertising practitioners to be adequately prepared for the future that awaits, advertising educators need to deepen their commitment to purposefully exploring race/racism and advertising with students. In this article, we highlight how a focus on critical reflexivity supports meaningful and lasting learning around race, racism, and advertising. Based on co-teaching an advertising and food justice course together since 2012, we outline a critical paradigm and four practices we use to foster critical reflexivity: acknowledging shared inheritance of racism, critical storytelling, deep listening, and kitchen table talk. In closing, we highlight considerations and challenges that often accompany teaching about race and racism, as well as the importance of self-care and debriefing for instructors. Throughout, we offer tools for cultivating a reflexive classroom that engages deeply and directly with issues of race and racism.