Historians of rhetoric have recently explored how nineteenth-century women’s personal and romantic letters have offered a venue for the rhetorical work of raising consciousness, building coalitions, and contesting gender norms. This essay examines the work undertaken by Lucy Stone and Henry Blackwell in their courtship correspondence. Drawing on a body of manuscript letters exchanged between 1853 and 1855 and a selection of nineteenth-century letter-writing manuals, the essay argues that the couple uses their letters to: explore their views on rhetoric; contest the genre and gender conventions being taught by manuals; and engender the possibility of forming a rhetorical alliance.