This article is about ambiguity in psychoanalysis, an ambiguity that is particularly striking in the psychoanalytic relationship between patient and analyst. The analyst is a professional in his consulting room, in his chair behind the patient, but he is at the same time a figure in the patient's realization of his inner world of objects. The analyst is a transference figure, but he is also a real person with his own inner private reverie and a subjective contribution to the analytic process. For some patients, the ambiguous analyst is an enormous challenge or threat. This article describes parts of the analytic process with one such patient, a man with an early history of severe trauma who at the start of his treatment completely denied this ambiguity and felt every reminder of his analyst being anything else but professional as a threat to his sanity. The author tries to show how the improvement of the patient's tolerance for ambiguity depended on the work done in the analyst's private reverie, a quite demanding process for the analyst.