The educated woman and the college girl were, for the great part of the nineteenth and twentieth centuries in India, subjects of immense anxiety. In this article, I examine the gossipy narratives that a missionary educator in South India, Eleanor McDougall, wrote biannually for readers in America and Britain, whilst she was Principal of Women's Christian College (WCC) in erstwhile Madras, along with the book on her experience that she eventually published. In doing so, I locate the circulation of gossip in transnational circuits as a site where colonial anxieties about young Indian women as subjects of uplift came to be produced. For women like McDougall, the expression of urgent anxiety about young women's moral and social conditions served as a means to secure legitimacy for the work they did, and position themselves as important participants in a new discourse of philanthropically mediated development that emerged in the early twentieth century with the influx of American charitable capital into countries like India. At the same time, I show, in responding to her writing about them, that the Indian staff and students at WCC did not concur with colonial authority marks a site of refusal: suggesting the anxious boundaries of colonial knowledge production at a time when the surety of discourses of racial difference was beginning to unravel. In its study of McDougall's gossipy writing, this article therefore contributes to a complicated and non-linear understanding of emotions as a site of power and hierarchy.