With a recurring focus on how his mother's tragic weaknesses and her compelling strengths affected his development, Awkward intersperses the chronologically arranged autobiographical sections with ruminations on his own interests in literary and cultural criticism. As a male scholar who has come under fire for describing himself as a feminist critic, he reflects on such issues as identity politics and the politics of academia, affirmative action, and the Million Man March.
By connecting his personal experiences with larger political, cultural, and professional questions, Awkward uses his life as a palette on which to blend equations of race and reading, urbanity and mutilation, alcoholism, pain, gender, learning, sex, literature, and love.