This essay attempts to analyse and discuss the difference between guilt and shame as depicted in The Scarlet Letter. Since the surrounding norms and conventions affect people’s actions, thoughts and feelings, it is necessary to take a closer look at the specific society depicted in the novel, which is that of Puritan New England. The first chapter, therefore, presents a description of the Puritan society. The Puritans lived by strict codes which encouraged the confession of sin and public repentance. The philosophical overview which forms the basis of the theme of guilt and shame to the novel under discussion is focused on the questions: what is guilt? what is shame? What are the differences between guilt and shame? Where do guilt and shame come from? Through the theories of different philosophers and psychologists it is argued that guilt arises from a negative evaluation of a specific behaviour, somewhat apart from the self. Shame is more about the quality of our person or self, which is found to be undesirable. In other words shame is about the self and guilt is about actions and laws. After having established a working understanding of some important aspects of what the conditions known as guilt and shame appear to be, the second part examines the nature and effect of these two terms, and the difference between the concepts through a detailed character analysis of Hester Prynne and Arthur Dimmesdale. These two characters experience guilt and shame, and the effects of the public’s opinion on their own personal sins.