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Both classical and contemporary psychoanalytic theories stress the importance of interpersonal dynamics in treating neurotic symptoms. Associations between the symptomatic and interpersonal level were formally represented in the symptom specificity hypothesis (Blatt, 1974, 2004), which linked obsessional symptoms to an autonomous interpersonal stance. Findings from cross-sectional group studies on symptom specificity, however, do not converge, possibly indicating that the complexity of associations is underestimated. This article presents a theory-building case study specifically aiming at refinement of the classical symptom specificity hypothesis by quantitatively and qualitatively describing the longitudinal clinical interplay between obsessional symptoms and interpersonal dynamics throughout a psychodynamic psychotherapy. Interpersonal functioning was assessed by means of the core conflictual relationship theme method (Luborsky & Crits-Cristoph, 1998). Findings affirm a close association between symptoms and interpersonal dynamics. However, obsessional symptoms proved to be determined by profound ambivalences—manifesting both within and between relationships—between dependent and autonomous interpersonal behavior. Psychodynamic interventions focusing on interpersonal conflicts were associated with symptomatic alterations. Conceptual and methodological considerations, limitations and future research indications are discussed.