In this chapter, Qrescent Mali Mason looks back at the ambiguous dimensions of the year 2020. Writing from the standpoint of a Black American feminist philosopher, Mason maps the ambiguities in Beauvoir’s work and life, and draws on the work of other feminist thinkers who are also complex, complicated, and brilliant. These ambiguities pertain, for instance, to Beauvoir’s love life and anti-racist politics, and are narrated in Mason’s auto-theoretical essay as a source of inspiration and ambivalence. Mason’s essay, and the lecture on which it is based, offers a pause to think about the ubiquity of the ambiguities that emerged in 2020 and thereafter. In both the essay and the lecture, the audience is explicitly invited to contribute their own ambiguities, thus enacting philosophy as a collective practice. ‘Ambiguity’ is hence an existential concept but also describes an ethical attitude, one that has helped Mason navigate a year that was itself full of ambiguities.