Scarlett O’Hara in Gone with the Wind has left a deep impression for her coping attitude towards romance, marriage and business. It is interesting that these three aspects of her life are more or less related to her flirtations with men. The characteristic language in those flirtations makes a perfect material for her personality analysis. In this paper, the flirtations by Scarlett in Gone with the Wind is analyzed in the framework of the conversational implicature and relevance theory with an aim to demonstrate how such violations of cooperative principle function in the characterization of the protagonist as well as the development of plot and theme. Ultimately this paper is to illustrate how such pragmatic analysis may contribute to literary criticism. Flirtation is the explicit violation of cooperative principle under which a traditionally successful communication is yielded. However, a large number of successful communications have also been found although they violate this principle, especially in literary works. Such violations are ideal materials to study the personalities of communicators. Through a detailed analysis of four classic violations of maxims, Scarlett’s personality in Gone with the Wind is scrutinized, social causes of such personality are explained and the novelist’s intention to promote women consciousness and independence is discovered.