This essay addresses challenges that emerged during Advent through recent experience of lecturing at Berkeley Divinity School, the Episcopal Seminary at Yale. For many of my students, Advent 2020 presented particular challenges since they found that the recurring utilization of ‘darkness’ as a metaphor for sin and death did not sit easily with their commitment to anti-racist thought and practice. This essay does not attempt to provide a definitive model for how Anglicans might engage fully with Advent themes, but serves as a paper to ‘think with’ in which the author (a) engages with Michael Battle’s work on Anglican spirituality and (b) describes how her own expertise on Gregory of Nyssa was brought to bear on present needs. The Advent focus on darkness and light, I propose, does not need to be circumvented but provides Anglicans who are attentive to the problems of racism with an opportunity to examine further their own approach to ‘darkness’.