This dissertation contends that North American culture is in the grip of a reductionism that neglects plurality while seeking after pseudo-universality and pseudoindividuality, exemplified by the apparently contradictory tendencies to take as normative what can be generalized and to deny universally applicable normativity. I pay special attention to gender stereotypes, in which the particular (individual) becomes irrelevant, ignored, or perceived as a threat unless it can be treated as part of the general (stereotype). I argue that philosophical fiction—and, in particular, young adult fiction— contributes to a principled plurality in both lived and academic philosophy. It does so through its imaginative power to enlarge perspectives, criticize from the margins, and galvanize readers to engage with injustice. I focus on young adult fiction because of its wide reach, relevance for ethical formation, and exceptional tendency to question stereotypical understandings of human existence. After explicating the distinction between lived and academic philosophy and situating my project in the larger conversation about fiction and philosophy, I argue for the ethical significance of philosophical interaction with story. In conversation with Martha C. Nussbaum and Hannah Arendt, I draw together three themes—the integrality of form and content, the ability of storytelling to act as critical thinking in context, and the key role of particularity in the context of plurality—in order to emphasize the need to approach fiction in its intrinsic plurality without losing the possibility of shared criteria. A causal model is insufficient in this regard. Drawing on Lambert Zuidervaart’s conception of imaginative disclosure, I show that art both suggests and requires interpretation and that fiction’s ethical contribution to philosophy needs to be understood as thoroughly hermeneutical. I settle on “narrative companionship,” a variation of Wayne C. Booth’s metaphor of stories as friends, as a helpful noncausal metaphor for interaction with fiction. Then I seek to demonstrate the fruitfulness of this metaphor, in contrast to academic philosophy’s traditional approaches to fiction as either a tool or an example, by commenting on several stories that have informed my own lived philosophy.