The Post-Civil War America ushered in a period when social and historical processes redefined the woman's role and choices. This work explores the process of negotiation between individual liberty and social convertions in the patriarchial and transitional American society of the nineteenth-century. The study focuses on the female protagonists in The Portrait of Lady and The Bostoniams which demonstrates that Heny James Placed women in the centre-stage in his fiction and watched them negotiating in the conditioning circumstances.