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This paper, written in honor of Sidney Blatt, explores how object relations are represented in narrative descriptions and in dream narratives and discusses how changes in these two assessments of object relations diverge or converge over the course of treatment. As part of Blatt’s Object Representation Research Group (ORRG) at the Yale University School of Medicine, Diamond and colleagues developed the Differentiation-Relatedness (D-R) Scale to assess the developmental level of mental representations as evidenced in spontaneous descriptions of self and significant others on the Object Relations Inventory (ORI). The D-R Scale focuses on self-definition and relatedness, the two developmental lines that in Blatt’s view drive the development and internalization of mental representations, in self and other. This study presents both clinical and extraclinical data on one patient, part of a larger sample of 40 who were systematically assessed for changes in D-R over the course of long-term psychoanalytically oriented inpatient treatment. In addition, this patient’s dream narratives were assessed for object relations with the Object Representation Scale for Dreams (ORSD). The results indicated that this patient moved from unilateral polarized or split descriptions of self and others on the ORI to more complex, balanced modulated and multifaceted descriptions at discharge (2 years, 9 months). Parallel improvements in the developmental level and quality of object relations were observed in the dream narrations. These changes suggest that transformations of the capacity to represent objects at both conscious and unconscious levels may be proxies for change in psychoanalytically oriented psychotherapy.