There has been increasing interest among analysts in the possibilities of enriching psychoanalytic thought through fuller incorporation of attachment theory and research. This paper offers a clinical illustration of the ways in which attention to an attachment perspective can lead to novel and useful ways of addressing the patient’s issues. It also presents a number of cautions that it is necessary to be alert to if attachment thinking is to achieve its full potential in advancing psychoanalytic thought and practice. Conceptions of attachment and approaches to its study and clinical use actually vary quite substantially. Some are more one-person, static, and categorical. Others are more two-person, dynamic, and focused on the process whereby attachment patterns develop and are maintained over time. This paper explores the distinction between these two versions of attachment theory and research with two aims in mind – first, to refine our understanding of the potential role that attachment thinking can play in advancing the psychoanalytic paradigm; second, to utilize the insights achieved through examining the attachment paradigm to consider some broader issues in the construction of psychoanalytic theory more generally and its relational variant in particular.