F. Scott Fitzgerald’s 1920’s novel The Great Gatsby shows that clouded judgments can lead to disappointments and heartbreak. Jay Gatsby, a rich man with a positive outlook, seeks to rekindle the past relationship he once shared with Daisy Buchannan. Refusing to accept that Daisy has already moved on, Gatsby is continuously blinded by the memories they used to share. On the first occasion in 5 years that Gatsby and Daisy have seen each other, Gatsby is extremely disappointed because, “he had been full of the idea so long, dreamed it right through to the end..at an inconceivable pitch of intensity. Now, in the reaction, he was running down like an over-wound clock” (92). Over the past 5 years, Gatsby has created a fantasy involving Daisy. After finally being reconnected, Gatsby is saddened by the fact that she does not live up to the image he has created of her. Gatsby gives Daisy a tour of his house in order to impress her. As the day goes on, it becomes evident that, “There must have been moments even that afternoon when Daisy tumbled short of his dreams- not through her own fault, but because of the colossal vitality of is illusion” (95). Although it is not Daisy’s fault, she has fallen short of the expectations Gatsby had for her. His illusions built up over time have begun to fog his apprehension of the differences between reality and appearance. Following the death of Myrtle Wilson, Nick warns Gatsby that he should leave town, but, “He couldn’t possibly leave Daisy until he knew what she was going to do. He was clutching at some last hope” (148). The last bit of hope Gatsby had was the slightest chance that Daisy would leave Tom. Again, his inability to recognize his harsh realities ends up being his downfall. Jay Gatsby, although an optimistic person, also is a very naïve man. Without the ability to accept how things truly are, he becomes very susceptible to heart break and disappointment.