This study explores the perspective of day school parents as they engage with questions of race with their children and in the context of their day school choice. We convened a book group in summer 2020. Nine White mothers of school-aged children met over four ninety minute sessions to discuss Margaret Hagermans' (2018) White Kids: Growing up with privilege in a racially divided America. The book served as a jumping off point for conversation about how participants experience race in their own lives, how they engage with race within the family, and how they understand their children's school to be engaging with issues of race. Hagerman followed families who chose mainly between public schools and secular private schools; our participants developed comparisons between Hagerman's schools and Jewish day schools, and between themselves and Hagerman's parents. While maintaining the uniqueness of the Jewish day school context, they also discovered commonalities with Hagerman's parents related to privilege and social class and the disconnect between good intentions and outcomes.