During a site visit in my role as faculty advisor for social work students, the ­supervisor began the discussion of a case by saying, “We are keeping an eye on this one. We think he’s a psychopath.” The female student then described a man who came to therapy so he could have a monogamous relationship. He described himself as having a sexual addiction, picking up men and women at a high-end department store, and using cocaine and Ecstasy on occasion. His presentation was narcissistic and grandiose, and he filled the therapy hour with expansive and disorganized stories. The student felt anxious and helpless as she attempted to engage him in discussing his presenting problem. This process seemed futile because he demonstrated no ability to reflect and seemed to convert every impulse into action. The concept of mentalization provides a useful framework for understanding and ­guiding interventions with clients like this one and assists with countertransferential reactions that may lead to therapeutic impasses (Fonagy, Gergely, & Target, 2008). The acquisition of a reflective mentalizing stance is a powerful developmental­ achievement that enables the individual to regulate affects, rather than using action and drugs to discharge feelings, as this client does.