Drawing on a sample of seven students (three Black, four White) from schools in the North before the Civil War, this article examines how schooltime writing—compositions, letters, and diaries—helped young women navigate social expectations and assert intellectual agency. While Black and White students’ expressions reflected different positionalities, both critiqued confining ideals of domesticity. White students challenged assumptions that their futures lay only in the home as wives and mothers, while Black students reimagined their place in intellectual and civic life, articulating visions of liberation and belonging that confronted racism and sexism. Building on Saidiya Hartman’s framework of everyday negotiations of power and William Reddy’s concept of emotives, the article shows how affective writing worked as a subtle mode of social critique. In doing so, it contributes to scholarship on women’s education and the history of emotions.