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There are some patients for whom otherness disrupts precarious experiences of personal coherence and stability. Analysts and patients are thus sorely challenged to find bridges between inside and outside, fantasy and reality, self and other, subjectivity and objectivity—the in-between spaces that give psychoanalysis its particular power. This article explores the clinical dilemmas in working with such patients who tend to present as either lost in subjective experience with little connection to externality, or as trapped in an objectified reality devoid of personal vitality. Winnicott’s conceptualization of transitional space, and Sheldon Bach’s elaboration of related capacities to move fluidly between states of subjective and objective self-awareness, are used to: 1) illuminate what’s missing in both presentations, and 2) describe the enactments that unfold between “me” and “not-me.” To the degree that its present, subjective experience is either disconnected from, or conflated with, externality. For patients without access to transitional space, its emergence will likely be from within these pathological organizations in which both members of the dyad struggle to keep inner and outer both separate and related.