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Addiction is notoriously difficult to treat. In this paper, I argue for the efficacy of a relationally analytic approach, as addictions often operate within malattuned, divisive relational contexts, providing a fleeting but vitalizing self-restoration. A debilitating subjective and intersubjective divisiveness often develops within such contexts, frequently marked by Brandchaftian accommodation and affective rigidity. Addictions are often derivative of such relational trauma—allowing analysts, with perseverance, experimentation, and perhaps some luck, to provide mitigation in a developmentally restorative context. I present a case study that highlights such a hard-won, mitigating relatedness, in employing an intersubjective-systems perspective. Obstacles arise from both the addicted patient’s compulsive aversions to vulnerability, any trace of “dependence,” and from my own co-transference. My own self-reflection reveals a discomfort with the patient’s rigid yet chaotic aversions against emotionality, and my subtle dismissal of his explanations of the importance of marijuana. He and his mother, meanwhile, struggle within an mutually enslaving system, demanding compulsive riddance of vulnerability and compliance from others—including the beleaguered analyst. Eventually the patient’s family context is seen to parallel my own archaically traumatizing environment, an analogous “hijacking” of authenticity. This difficult stretching of reflectivity, together with some of my own personal experience with addition, leads to my own differentiation from transferential rigidity. A dyadic loosening occurs, with a reinforcement of the analytic frame, and my deeper understanding of the patient’s dilemma; this recognition frees the patient to self-initiate steps towards expansiveness, easing his compulsive reliance on antidotal and isolating self-protections.