In this article the author explores what is involved when working with dream material in a clinical setting. She starts with the difficulties Freud encountered in the Interpretation of Dreams when attempting to discuss this complicated material in a concise way. This leads the author to the matter of the interpretation itself. Using several of Freud’s articles she explores different approaches to the concept of interpretation and confronts the reader with some of Freud’s ideas on working with dreams. The theoretical part of the article concludes with a brief discussion of the Lacanian vision of interpretation according to Fink. This is followed by a substantial clinical section illustrating this theoretical material, using the case of a woman whose mourning process over the sudden death of her husband is problematic. Her dreams form an important part of the analysis in this case. The author concludes by elucidating in detail one session with the patient in which not only the ambiguity of meaning in dream material, but also the choice of a specific interpretation and its effect, is demonstrated.