Why people trust is a question that has preoccupied scholars across many disciplines. Historical explorations of trust abound, but we know relatively little about the workings of trust in the history of investment. Despite becoming increasingly mediated and institutionalized in the nineteenth century, the market for stocks and shares remained local and embedded in personal relations to a significant extent. This created a complex trust environment in which old and new forms of trust coexisted. Investors sought information from the press, but they also relied upon friends to help them navigate the market. Rather than studying trust in the aggregate, this article argues that focusing on the particular allows us to appreciate trust as an emotional and ultimately imaginative process depending as much on affective stories as rational calculation. To this end, it takes the case of a Bath clergyman and workhouse schools inspector, James Clutterbuck, who solicited investments from a wide network of friends and colleagues in the 1880s and 1890s. By capturing the complex interplay of friendship, emotions, and narrative in the formation of trust, the article offers a window onto everyday financial life in late Victorian provincial England.