In today’s modern urban environment, people often emphasize speed, productivity, and surface-level connection and communication within society. However, in this type of urban environment, the genuine connection between people with each other and the connection between people and the natural environment slowly fade away. Therefore, this project explores how these types of alienation and isolation caused by the urban society and urban environment are revealed in specific examples across all ages and different cultures. Inspired by T.S. Eliot’s The Love Song of J Alfred Prufrock, this project will be tightly connected to the alienation Prufrock experienced, including social alienation during the party, psychological isolation when being afraid of making a decision, and how the overall ghostly and foggy urban environment impacted Prufrock. Eventually, this project will end with a proposal showing how people should create a more genuine connection with each other in society and how sometimes people should engage with the natural environment more and appreciate nature.