This thesis explores the relationship between philosophical content and literary form in Anglo-American political theory. The Anglo-American tradition is dominated by analytical approaches to philosophical objects that cannot adequately conceptualize ambiguous elements of lived experience. To do so, the study of political theory should include means of philosophizing that embrace ambiguity, such as Simone de Beauvoir's literature. This thesis takes Beauvoir's essay The Ethics of Ambiguity and novel All Men Are Mortal as case studies in how to theorize about ambiguous concepts. It applies a combined literary and phenomenological approach to reveal how her literary devices simulate our experience of ambiguity and freedom. It contributes to discourses on ethics and the relationship between form and content while serving as a model for research in political theory interested in alternatives to analytical approaches and the pursuit of experiential truths.