This paper studies Leopold Bloom’s social isolation and detached personality through the lens of neurosis in James Joyce’s Ulysses. To achieve this, this paper draws on Karen Horney’s theory of neurotics, in which people with detached personality feel as though they do not belong among other people. Such neurotics not only separate themselves from others but become alienated even from themselves. According to Horney, three neurotic elements lead to the formation of a detached personality: the need for “self-sufficiency,” “perfection,” and “narrow limits in life.” In Ulysses, Bloom distances himself from other people because of his anxiety and his desire for freedom, which results in his social alienation. To deal with his isolation, Bloom needs to flaunt his superiority, prove his independence, and set limitations on his life to relieve the pressures imposed on him by people and society.