Virginia Woolf once remarked that Dorothy Osborne’s fear of ridicule was “scarcely sane.” It was one reason why Osborne never published a line during her lifetime. Yet Osborne, a seventeenth-century English writer of vivid letters, had a playful sense of humor, which she used to reframe expectations about women’s role. She was far from the only woman to turn notions of male superiority into play—even in a culture where laughter was also used to enforce gender norms. Survival of women’s joking letters is largely limited to the gentry, but glimpses of other women’s jests appear in court cases and other sources. It was often a privileged, intimate relationship with a male partner that enabled the women to joke, as in Osborne’s letters to her lover. Laughter between lovers was widely assumed to be normal, and, conversely, laughter was sometimes viewed as a sign of such intimacy, or even of sex itself. Female laughter, especially, drew suspicion from moralists, but their complaints seem to have been widely ignored. Public culture was full of anti-female stereotypes, and those who flouted gender rules risked public ridicule. Yet within intimate relationships, even the stereotypes could become a joke.