Theo, a self-described “unmarried, childless, thirty-seven-year-old ex-bookstore clerk,” finds himself unmoored and shaken when his best friend, the successful writer Charles, dies of a drug overdose in New York. Introverted, raised by a cautious grandfather after his mother’s abandonment, and always secretly jealous of the charismatic Charles, Theo finds solace in the fictional world of comic books, art, and the gritty Harlem whodunits of Hyman Chesnutt. Dissatisfied with the explanation of Charles’ overdose, Theo takes on the quest of finding the real answer. Along the way, he must grapple with the fundamental questions of life: Who is he, and what does he want? Theo’s quest for truth is interspersed with revealing flashbacks, unfolding the layers of who Charles actually was versus who Theo thought he was. The story’s main tension centers on alienation versus connection, a fitting theme, given the title’s allusion to T.S. Eliot’s “The Love Song of J. Alfred Prufrock.” The story’s structure gently mirrors Hyman Chesnutt’s detective novels that Theo loves. Creating a story about the search for meaning can sometimes make a protagonist appear self-absorbed, simply because the focus is on a single character’s thoughts; however, this narrative treats every flawed and frustrating character (with the exception of the antagonists) with deep compassion as each experiences loneliness and seeks connection. The story and tone are both somber, though the novel displays sparse humor during ironic situations in which characters misunderstand one another. Readers looking for a high-stakes mystery will likely prefer other reads, but those who love to probe the internal life of characters will enjoy this poignant story.