F. Scott Fitzgerald chronicled the 1920s America as accurately as he recreated the ‘flapper heroine’. The flapper was distinctly unique with her ‘romantic individualism’, rebellion and sexual liberation to become the female representative a new social order. She was also seen as the symbol of conflict, moral anarchy and ‘decline of the west’. Flapper was celebrated and a celebrity of a youth culture of that period. The flapper heroines invited as much criticism as the attention of the nation. It was easy to criticize the ‘popular daughters’ like Rosalind, Isabelle and Eleanor in This Side of Paradise for their ‘moral dissolution’ than to praise them for their confidence and courage. It was easier to call Gloria in The Beautiful and Damned as ‘American bitch’ than to see her dignity in the face of crisis. Daisy in The Great Gatsby was a true product a corrupt society but as readers we never studied her with sympathy to know her mind, the façade behind her artificiality. So is Nicole in Tender in the Night whose real persona is suppressed behind her madness as she is handed over from one male hand to another. Fitzgerald throughout his literary career delineated a wide range of female characters in his later novels with all their complexities in the backdrop of a great social flux. He was from the beginning ambivalent towards his female creations. On the one hand he was completely fascinated with these beautiful and bold characters and equally repelled by their ‘chilling selfishness’ and ‘high-handedness’ and so were his readers and critics. She was condemned as vamps, leeches and idlers. This book attempts to discover the inner core of these much talked about heroines, their struggles, sacrifices and moral integrity. The book tries to delve into the minds of these social transformers to find their insecurities and vulnerability in a strong patriarchal order. This book discovers the New Woman’s power to be her own person and her journey from weakness to strength. The book makes an attempt to tell the readers the other side of the story.