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Many patients seen today use sophisticated capacities for psychological reflection and premature synthesis to ward off knowledge of more primitive conflict and islands of unintegration. They show a precocious talent for free association, a talent they perversely misuse. Similarly, they enjoy access to a rich fantasy life, even as they subtly impoverish it. Effective therapeutic work requires that they suffer “traumatization”—experiences of dedifferentiation that undermine their considerable capacity to know what they feel and think. Structural and process variables interact with content variables in complex and ambiguous ways. As a consequence, estimates of the authenticity and “fit” of personal and interpersonal experiences and behaviors of both partners in the therapeutic encounter become necessarily involved. Such factors may increase the possibility of misunderstandings, but also of more authentic and firmly grounded understandings. Similar issues are eventually revealed in these patients' early lives, where psychological and other formulaic understandings were prematurely applied to offset overwhelmedness and other unarticulable experiences; the patient's talents for ambiguity, irony, self-soothing, or responsiveness to others were, in effect, exploited at the expense of full psychological growth. Versions of this clinical presentation may be increasingly common in a new generation of analyzable patients. Clinical work with them is facilitated by a synthesis of contemporary developmental, structural, and object relations theory.