Individual choice is a central feature of the psychological portrait drawn by nearly every established school of thought in modern American jurisprudence. Legal scholars are increasingly interested in piercing the conceptual surface of choice to inquire into its actual psychological workings. The study of choice in this emerging behavioral legal scholarship draws primarily from cognitive psychology. This article argues that this important inquiry into choice should be broadened to include modern psychoanalytic ideas about imagination. An example of the importance of a psychoanalytic perspective on imagination is provided by the law governing the enforceability of prenuptial agreements. As this discussion illustrates, psychoanalytic psychology, in conjunction with research from the cognitive sciences, provides a valuable framework for examining assumptions about individual choice in law.