This paper investigates women's learning experiences in the Confucian tradition and the social dismay and stigma associated with them. Despite being considered a meta-virtue in the Confucian tradition, learning becomes rather complex when women are the learners. It is viewed by learned women as a curse rather than a blessing in pre-modern China; it is associated with the stigma of “leftover women” and “the third sex” in contemporary China. Based on an examination of works written by women thinkers, I argue that the asymmetry in social recognition for men's and women's learning is rooted in the social and family structure of nei (in) and wai (out), which does not assign sufficient cultural and moral significance to learning achieved in the nei domain nor permit its continuous and accumulative existence. I propose two preliminary steps to rectify the issue of the lack of social and moral recognition of women's learning: first, a reforming of the nei and wai structure to allow assigning more moral, cultural, and normative significance to affairs in the nei domain. Second, re-examine and utilize classical Confucian texts such as the Mencius and later works by women writers to support and guide such reformations.