Woolf's novel, Mrs. Dalloway, is widely recognized as a work of modernist literature that incorporates key modernist features such as psychological depth and skepticism. Throughout the novel, Woolf presents readers with depictions of characters that exemplify skepticism and a focus on reality. The objective of this thesis is to elucidate the skepticism experienced by the characters. The researcher employs a structural methodology to examine the characters, plot, setting, and themes present in the novel Mrs. Dalloway. In order to establish the relevance of the context to the thesis, the researcher employs the concept of skepticism to expound upon the origins of skepticism experienced by the characters and the resultant effects of such skepticism on their personal lives. The main goal of this thesis is to conduct an analysis of the concepts of psychology and skepticism in Mrs. Dalloway. This will be achieved by examining the characters of Clarissa Dalloway and Septimus Warren Smith, both of whom exhibit traits of skepticism. The study will focus on identifying similarities between these characters. The present thesis delves into the topics of social validation, matrimony, conflict, and institutional confidence as byproducts of civilization. Upon conducting an analysis of the aforementioned novel, the researcher has determined that skepticism can be discerned through the medium of literary works. The researcher additionally delineates the adverse effects on the mental and physical well-being of the characters.