Abstract
This study theorizes that there are three essential, often unconscious, clinical components that may perpetuate homelessness among the chronic homeless population. The three main dynamics are a conflict with the familiar experience of homelessness, difficulty with structured environments, and an adaptation to the lifestyle of homelessness. These dynamics highlight a paradox for many who are chronically homeless: the desperate desire to leave their life of homelessness versus the deeply familiar and entrenched state of homelessness that serves to keep them homeless. Existing psychoanalytic theory is used to examine case studies that are drawn from clinical observations in the field. This article concludes that, as a result of these powerful dynamics, successful placement into long-term settings is predicated on two crucial aspects of service delivery: the establishment of the therapeutic relationship and the availability of low-demand supportive housing.