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Having first established that “The Unfortunate Happy Lady: A True History” has been subject to very little critical analysis, this article discusses how the protagonist, Philadelphia, breaks the conventions of society in incremental steps, through rebelling against the situation in which she finds herself. Philadelphia ultimately decides who she will marry; however, before reaching this peak moment the “unfortunate happy lady” follows traditional customs, contracting a marriage orchestrated by other people. Several episodes of female agency will be explored, following the evolution of the protagonist from oppression by a male authority figure towards redemption, presenting Philadelphia as an independent and decisive woman, capable of maintaining her virtue and her moral integrity. The article will examine the writer’s use of irony. Literary influences on the text will also be examined, such as the parallel between a poem by Ben Jonson and a key episode in the narrative.