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The present paper is an attempt to explore the actual and potential convergences and divergences of the ontological-existential philosophy of Martin Heidegger and Freud’s analytic thinking as well as later developments in psychoanalysis. The first part of the paper compares and contrasts Freud’s and Heidegger’s thinking on issues of truth and anxiety, which are central to their respective doctrines and highly relevant to working with difficult patients. It is shown that both Freud’s psychoanalytic theory and Heidegger’s ontological philosophy stress the process of opening up to the anxiety-evoking truth and the individual’s responsibility to uncover the truth as a source of freedom. The second part of the paper examines the impact of Heidegger’s thought on the psychoanalytic understanding of individuals with severe character pathology, on the spectrum from malignant narcissism, through perverse organizations, to psychosis. In this context, the authors discuss the notion of ‘anxieties of being,’ a shift towards a more ontological psychoanalysis and the phenomenologisation of psychoanalytic language. Viewing people as interpretive creatures, the authors believe that Heidegger’s hermeneutic outlook may enable psychoanalysts to approach their patients in a more open and accepting manner.