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Historically, psychoanalysis has failed to differentiate adequately between aggression and assertion. It is uncontroversial to state that bullying is a form of aggression. However, if aggression and assertion are not adequately distinguished, bullying could also be viewed as a form of assertion. Some psychoanalysts have attempted to resolve this by using the terms aggression and assertion as synonyms but introducing the notion of nondestructive aggression. Bullying, then, is understood to be hostile aggression or hostile assertion. In this article, I aim to prepare psychoanalytic and philosophical groundwork for a meaningful differentiation between aggression and assertion, and, at the same time, to shed light on the nature of bullying, parental bullying in particular. To achieve these aims, I critique an aspect of the case material presented by Frank Summers in his (2005) book, Self Creation: Psychoanalytic Therapy and the Art of the Possible. I also critique Parens' (2008) notion of nondestructive aggression as used by him and by Summers. Additionally, I discuss some of the philosophical notions Summers introduces and discusses relevant to a critique of his notion of the analyst's vision of the patient's development in its relevance to his case of Anna.