Questions about gender identity may seem to be characteristic of our time, but others have gone before us in challenging societal roles. From Harriet Freke in Maria Edgeworth's Belinda (1801) to the real life Chevalier d'Eon, men and women have been pushing the boundaries of what it means to be male and female. Where does Jane Austen come in this debate? How would she negotiate current questions about how we engage with our gendered social roles? We go from Lady Susan to Persuasion in our quest for some of the answers.