As a deep reader of nonfiction prose and theories of nonfiction, my influences are too many to mention, but two bracing, speculative essays by Cynthia Ozick and Russian cultural theorist Mikhail Epstein constitute an interlocutory space for the form and movement of Awkward: A Detour, which is not after all a book divided into chapters but a book-length essay. In light of the revitalization of the essay in the past decade, I am moved by Cynthia Ozick’s “She: Portrait of the Essay as a Warm Body” (in Quarrel & Quandary) and Mikhail Epstein's "An Essay on the Essay.” The essay is neither a polemic, nor a tract, nor an article according to Ozick, but the “movement of a free mind at play.” It has an “interior heat”; an essay is “a way.” The finest essays move among discourses: for Ozick, from reality, toward memory, dreamscape and back again; for Epstein from documentary (description) to fiction (imagination) and theory (speculation). For my own part, I like to think of essays as workshops for making, breaking, and reinventing order. For Epstein, the essay has a “nomadic and transmigratory essence.” In his “Essay on the Essay,” he describes the essay as a literary hybrid, characterized by digression, by surrender, and by weakness. (To paraphrase Gertrude Stein, and in agreement with her: “I do not write in order to be right.”) The essay is a kind of reparative act that isn’t closed; notes Epstein, “Essayism [his coinage]…unites fragmented portions of culture. But in so doing, essayism leaves enough space between them for play, irony, reflection, alienation and defamiliarization,” and “The essay is held together by the mutual friction of incongruous parts that obstruct one another.” Ozick speculates that an essay does not persuade but coerces assent, it “courts agreement” without requiring it. Epstein seems to echo Ozick since, for him, “Two conditions must be met in the essay: audacity of vision and awesome respect for things themselves,” or “boldness of proposition and meekness of conclusions.” Though I I am moved to question the ideological implications of Ozick’s and Epstein’s claims—i.e., what does it mean to turn the essay into a repository for fantasies of freedom?—I composed Awkward: A Detour with an eye toward wandering, exploration, and play. If I followed “awkwardness,” where would it take me? This is a question that I asked. Awkward: A Detour neither establishes nor demonstrates an argument per se, though it is keen to recover “awkwardness” for its untapped and radical potentialities. This is what it is trying to do.