In Taiwan, traditional norms of womanhood are deeply rooted in Confucian ideals that emphasize filial piety, marriage, and reproduction. Women are generally defined in relation to their roles within the family, and those who operate outside of these norms—such as Buddhist nuns and sex workers—are frequently marginalized. These women are particularly visible because they deviate from the expected life trajectory for Taiwanese women, yet they are remarkably rare and receive limited scholarly attention. This paper explores how these two groups, though extremely different in lifestyle and public perception, challenge prevailing definitions of Taiwanese womanhood by existing outside of expected familial and gendered roles. Drawing on legal history and personal narratives, this paper analyzes how both Buddhist nuns and sex workers are conditionally accepted by the country based on their perceived utility to national or familial interests. While Buddhist nuns have gained broader acceptance due to their alignment with values like charity, cultural preservation, and international diplomacy, sex workers remain criminalized and stigmatized, despite often serving as primary providers for their families. The instability of their legal and social status reveals how Taiwanese society continues to discipline non-conforming women based on fluctuating political and economic interests. By centering the lives of Buddhist nuns and sex workers, this paper complicates the dominant narratives of gender and progress in Taiwan, showing how womanhood is still tied to patriarchal expectations, even in the context of apparent autonomy or resistance.