This chapter repositions ideals away from their role as defensive structures restraining aggressive and lustful drives (as traditionally viewed) toward their place in shaping creativity and love. We select and mold our particular ideals in providing meaning and in this manner help to create those selfobjects needed to resolve or soothe our needs. This creative process may include “reshaping” of the available object to represent the “idealized other.” From this perspective, Kohut's view of idealization and the idealized parental imago will be considered, including my own notion of a one-and-a-half person psychology. Our ideals inevitably conflict and clash, leading to internal self-conflicts that generate what I call the dialectic of narcissism. Narcissism is here considered broadly, reflecting all attributes of self-experience. Shame plays an important role in this dialectic, relating to failure with regard to ideals and to falling short of cherished goals. Ultimately, it is the shaping of, and approximation to, flexible and meaningful ideals that comprise that lofty, ineffable, human ideal—wisdom. Clinical vignettes will be offered to illustrate these themes.