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Most activities in society are measured with respect to whether they involve a step forward. This ideal of a forward movement lingers over most accounts of the history of psychoanalysis as well. Joel Whitebook’s biography is no exception. By juxtaposing his much-acclaimed work to the ones of Wladimir Granoff and Lou Andreas- Salomé I want to discuss whether it is so that the evolvement of psychoanalysis is marked by a steady growth of knowledge. To amplify this question, a triptych is chosen as the form of presentation: Three analysts from different epochs, put side by side. Each relates differently to the fact that psychoanalysis has its point of departure in Freud’s singular experience. Accordingly, they also depart in their view on sexuality and femininity, indeed, still, a terra incognita. A key to this disaccord, however, is not the idea of psychoanalysis moving forward culminating in Whitebook’s biography. It rather prompts a reflection upon what widening understanding really amounts to, indeed a reverberating question, as it reveals itself not only in writing the history of psychoanalysis but as well with each analyst confronted by hardly explainable phenomena. Too ambitious theories may divert us from this task.