The theme of this paper is to occupy the liminal spaces of what constitutes “acceptable” scholarship on gender and sexuality in the premodern Islamic world. First, it pushes the boundaries of MESA by carving a space for South Asian scholarship in ways that can allow for comparative engagement with the SWANA regions. Second, it employs unorthodox methodology in its analysis of the Urdu ghazal, by reading a form of subjectivity and agency in a formally rigid genre. Lastly, it challenges normative understandings of autobiography by extending the threshold of literature to acts of performativity. All of the above are possible through a deep analysis of the tawaif, or courtesan of premodern South Asia, and the body of literature written by and about this influential figure. In the first part of my paper, I set the mise en scène for the South Asian courtesan, one which emphasizes acts of resistance and erotic manipulation through the cultural production of poetry, music, and architecture. This anti-imperial historiography about courtesans allows the opportunity for poetry to function as a vehicle of social and physical mobility for premodern women. I examine the kotha, or bordello, as a space where female sexuality is fairly constructed by women and associate the poetry of the courtesan through Bakhtin’s concept of the chronotope, to distinguish the imagined spaces described in ghazals with actual physical spaces that the courtesan was able to travel. Next, I problematize the gendered voice in Urdu ghazals and illustrate how tawaifs wrote in masculine voice to invert gender norms of the time and to challenge alternative patronizing genres in the feminine voice. In my opinion, the manipulation of erotic and devout imagery in the ghazal, combined with direct solicitations, show a particular agency that traditional literary scholars may overlook. Lastly, I challenge the genre of the autobiography by constellating architectural sites, courtly performances, and gift giving to create a more inclusive picture of who these women were. Based on deconstruction theory, I argue that poetry is another instantiation of autobiographical work as it is a performance of selfhood. An inquiry into poetry as autobiography may seem theoretically unorthodox, but this is an exercise in anti-assimilationism for the pre-modern courtesan and for the scholar who studies her.