During the Ming Dynasty (1368-1644), the pleasure quarter played a crucial role in the bustling cultural scene of the southern capital Nanjing. The elite courtesan Ma Shouzhen (1548-1604), also well known by her style names Xianglan (Orchid of the River Xiang) and Yuejiao (Lunar Beauty), 1 was a famous painter and poet who lived in the Nanjing entertainment district along the Qinhuai river ( Figure 1). In the late Ming period (1550-1644), courtesans, who were 'highly educated, creative and skilled' women at the top of the entertainment industry in the main cities, 2 achieved great esteem for their writing and painting skills as well as they embodied values of culture, chivalry and nostalgia. 3 In the Chinese Empire, where women were not officially allowed in the public sphere of bureaucracy and where Confucian patriarchal values idealised the role of the wife in the house's inner quarters, the courtesan represented an extraordinary negotiation of gender and space boundaries. This article is concerned with the study of visual and textual sources by and on the courtesan Ma Shouzhen as extremely valuable material for the investigation of the interplays of gender and space in early modern Nanjing.The remarkable work by Catherine V. Yeh, which explores the role of courtesans in the urban space and the entertainment culture of modern Shanghai at the turn of the twentieth century, 4 is one of the few instances in which the secondary scholarship deals with the agency of women in the cityscape. The research on Chinese cities lacks a proper understanding of women in the urban space, and the construction of (gendered) space in a pre-modern or early modern context still needs to be further investigated. 5 This article, by considering the example of the elite courtesan Ma Shouzhen, contributes to understanding the engagement of courtesans with the space of the Nanjing pleasure quarter in the second half of the sixteenth century. Space is not only related to geography, it is 'the product of relations which are active practices, material and embedded, practices which have to be carried out, space is always in a process of becoming. It is always being made'. 6 In order to understand those social relations and practices occurring in the space of the Nanjing pleasure quarter, I employ gender as