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Using Winnicott’s theory, this article produces an account of the individual’s relation to a given conceptual framework. Whereas Winnicott’s ideas have been almost exclusively discussed in developmental and psychopathological contexts, the present article extends Winnicott’s theory and applies it to the problem of interpersonal understanding. Taking a lead from one of Winnicott’s letters to Klein, the article investigates the problem of expressing one’s idiosyncratic insights in the confines of a given conceptual framework. The article examines Winnicott’s theory of compliance and creativity, discusses the plea that Winnicott makes to Klein, analyses the encounter with a “dead language”, and investigates the asymmetrical structure of interpersonal understanding. Cashing out the latter in terms of an “illusion of contact”, the article enhances our interpretation of the successes and shortcomings of interpersonal …