A vexing clinical moment with an addictive patient provokes the author’s “inner-Bogart” voice, a cynical wise-guy persona confirming the author’s sometimes pessimistic perspective, clouding his usual relationally empathic sensibility. After attempting and failing to rebuff such pessimism, he turns to writing, where he recalls a childhood love of film noir and the poignant family memories associated with it, transforming him from a frustrated therapist into a detective seeking “clues” about the case. He discovers unseen parallels in his own upbringing with alcoholic caregivers, who seek the “bottom line” of their own protection at the expense of their children, reinforcing his smart-alecky pessimism. By integrating his “inner gumshoe” via analytic writing, he finds that his patient shares his black humor. This loosens their mutual tension and frees up the patient’s authentic affectivity. The initial tension now leads to a cocreated alliance, the author hoping the patient will Say it again, Sam.