This is a creative writing thesis comprising of novel and critical commentary. The overall aim of both parts is to engage with the dual topics of female agency and queer choices in the late eighteenth century. The novel, A Chequered Scene, transplants a sixteen-year-old girl from the twenty-first century to 1790 Hampshire, thereby highlighting the contrasts and similarities experienced by women and queer people in the two time periods. The novel aims to deliver an authentic portrait of eighteenth-century life through its style and language, as well as capture the sense of the eighteenth-century novel through its split narrative, epistolary structure. A Chequered Scene explores and illuminates the liminal spaces within which women and queer people exercised their agency. This is done through the narrative itself and in the creation of specific characters whose lives are representative of the potential opportunities or strictures their historical equivalents may have faced: the young heiress with a mercenary suitor; the rich widow who relishes her liberty; the ‘fallen woman’ with an implacable devotion to the one she loves; one born to the wrong sex who dons the clothes of their chosen identity. Part two, the critical commentary, offers a series of demarcations on the core aspects of female strictures in the late eighteenth century, including marital prospects and potential careers. Claims for originality lie in the production of an original novel and in employing the extended metaphor of life as ‘a chequered scene’ in the commentary. Queer and female lives navigate the board of society, either staying within the light of patriarchal strictures, or straying onto the dark of impermissible proclivities. Research into the collection at Chawton House, particularly educational works, conduct literature, memoirs, and diaries, as well as building on recent criticism, has informed the creative aspect in an original way.