This chapter examines the relationship between time, feeling, and gender in two foundational texts of the Scottish Enlightenment, the Ossian poems and Adam Smith’s Theory of Moral Sentiments. It contends that Macpherson and Smith created a temporal map of emotion that gauged social development from “primitive” to “developed” cultures and offered women writers and Scottish philosophers a new field upon which they could experiment with the relationship between gender and historical progress. Despite their obvious differences, Macpherson and Smith used women’s social status and the feminine values they were thought to impart to their male counterparts as tools for charting, evaluating, and questioning emerging theories of historical change. The ambiguity surrounding feminine sentiments’ placement in these Scottish Enlightenment narratives of historical progress creates the foundation for the following chapters, which trace women writers’ engagement with the theories of feeling and historical progress articulated by these two influential writers.