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Contemporary behavioral legal scholarship on individual decisionmaking draws primarily from cognitive psychology. This Article argues that the field of behavioral legal scholarship should be broadened to include modern psychoanalytic ideas about the processes of individual decisionmaking. As explained here, the basic perspective of psychoanalytic psychology is largely compatible with recent cognitive research on decisionmaking. However, a psychoanalytic perspective adds valuable nuance and complexity by exposing for scholarly examination certain essential attributes of individual decisionmaking that have so far been overlooked. As a first step in bringing modern psychoanalytic ideas to the attention of contemporary behavioral legal scholars, this Article examines imagination, a psychological attribute central to individual decisionmaking and a fundamental feature of psychoanalytic psychology. Contemporary legal scholarship recognizes the relatively narrow idea of a cognitive imagination by looking at processes such as representation, memory, and counter-factual thinking, as well as cognitive distortions and biases in processing information such as the availability heuristic. In contrast, imagination as understood from a psychoanalytic perspective is the creative capacity to express one’s personal wishes, needs, and desires in words and images. Imagination is central to decisionmaking because, however trivial or important the context, individual choice always depends fundamentally on consideration of desired future courses of action and their consequences. For this reason, studying the origins and mechanisms of imagination – its relationship to reality testing, its sources in early childhood, and its unconscious operations – is essential if law is to develop a comprehensive understanding of individual choice. An example of the value of psychoanalytic psychology to contemporary legal scholarship is provided by examining the law governing the enforceability of prenuptial agreements. As this discussion illustrates, a psychoanalytic perspective, in conjunction with research from the cognitive sciences, provides a richer understanding of the assumptions about individual choice upon which many laws and legal policies are based.