This dissertation will explore F. Scott Fitzgerald’s fiction as valuable texts of the Jazz Age,
evolving with each of the societal challenges he presents through his flirtation with failure
and the concept of the hopeless romantic. The sense of failure woven through his literature is
the main attraction of his craft, which I argue is most prominent aspect of his writing’s legacy
in the decades after his death. The texts in focus are This Side of Paradise (1920), The
Beautiful and Damned (1922), and The Great Gatsby (1925), which depict the development
of his fiction throughout his career and the events of his life, from his optimistic youth to his
disillusioned middle age. More importantly, the analysis of these texts reveal the evolution of
the hopeless romantic and the misconception of love, whereby the inability to sustain
romantic connections suggests their incompatibility with society. Each novel features a new
perspective of love conceived by the hopelessly romantic protagonist: egotistic, materialistic,
and idealistic, all of which are misconceptions born from the unstable society where
superficiality prospers. Exploring the development of the romantic hero and their hopeless
relationship with love will demonstrate the nature of society and its downfalls. As well as
this, it will reveal the complexity of Fitzgerald’s fiction, which resides in a paradox between
longing for love with all the substance it entails, and understanding that he can never capture
it. Therefore, as much as Fitzgerald became a celebrity of the Jazz Age, he also used his
career as a writer to criticise the period’s increasing disparity from reality and substance,
represented through multiple romantic affairs he writes, like his own, which inevitably crash
and burn.