This article explores how older White Dutch people produce reflexivity on race and racism in the context of the public controversy around the “Zwarte Piet” (black Pete) tradition. Reflexivity refers to a conscious effort to become aware of and address one’s unconscious biases. Fourteen semi-structured in-depth interviews with older Dutch White individuals (65+) from (suburbs of) big to medium-sized cities located in the Netherlands were qualitatively analyzed with a combination of thematic and critical discourse analysis. We found that participants reflexively engaged with race and racism within three discursive contexts: (1) generational (dis)connectedness, (2) ever-evolving public discourses, and (3) identity (re)considerations. Across these contexts, the production of reflexivity entails rapid shifting from openings for critical reflection to epistemological and ontological anxieties. We show how the avoidance strategies offered by hegemonic Whiteness discourses offer comfort and perceived escape routes from such anxieties, while also creating new uncertainties for our participants.