Mary Wollstonecraft was both a writer and a fierce critic of what we now loosely define as “conduct literature.” In one of the most powerful chapters in A Vindication of the Rights of Woman, her searing “Animadversions on Some of the Writers Who Have Rendered Women Objects of Pity, Bordering on Contempt” focus particularly on two of the most popular advice texts of the period, James Fordyce’s Sermons to Young Women (1766) and John Gregory’s A Father’s Legacy to his Daughters (1774). But her first publication, Thoughts on the Education of Daughters (1787), was in many respects an orthodox piece of advice writing. Indeed, some passages in Thoughts strongly echo Gregory’s views, and Wollstonecraft included several excerpts from his writings in her anthology The Female Reader (1789). These perhaps unexpected continuities are a valuable reminder of the wide spectrum of texts and writers offering guidance on girls’ and women’s education and behavior in the eighteenth and early nineteenth centuries, and of the danger in making ahistorical assumptions about their identity and effects. At the same time, the shifts in Wollstonecraft’s engagement with Gregory indicate her increasingly sophisticated alertness to the workings of textual politics and provide insight into the radicalizing effects of French Revolutionary ideas on her intellectual development.