Stories of people assigned female at birth donning men’s apparel and joining the military or going to sea were common in early modern Europe. This phenomenon has been widely written about, particularly in popular maritime lore. The most common storylines involve a woman who followed a male lover to sea or went to war for their nation. Many people knew transing gender was something done successfully for generations and this knowledge was a strong inducement for some to try it. Poor people assigned female at birth presented themselves as men to improve their opportunities to earn a living and/or to resist the social restrictions placed on women’s lives. Life in eighteenth-century England for a working-class woman meant low wages, political powerlessness, and the constant threat of violence, including rape. But we must remember that social and cultural expectations of gendered behavior were rather strong, preventing masses of women from assuming a male identity. To transform oneself and one’s life into something completely different than what one was taught, to move among strangers seeking friendship and community, never knowing if or when they might turn on you, torture you, or turn your life upside down – all of this was too much to expect of those who were merely bored or simply poor.