This dissertation contributes to the nascent study of the Tamil Can˙kam corpus, a collection of poetic anthologies produced in the first three centuries CE. The Can˙kam poems are constructed around the two complementary themes of the "inner world" relating to emotions, romance and family life, and the "outer world" relating to kingship, warfare and public life. This dissertation argues that the thematic division within the corpus is gendered, as the "inner world" is associated with the feminine while the "outer world" is associated with the masculine. Each chapter explores the way that the poets establish the boundaries of femininity and masculinity through both the form and content of their verses. This dissertation focuses closely on the moments of rupture in the poets' system of gender construction, for these moments suggest that the poets acknowledged that gender is more fluid and complex than it initially appears. To better understand the workings of gender and sexuality in these poems, this study juxtaposes recent theoretical frameworks with these poems from the distant past. Methodologically, this dissertation collapses traditional historical time, bringing the ancient Can˙kam anthologies into conversation with ideas that are circulating now. In doing so, it seeks to elucidate both the poems and the theory, while also opening up new questions in both fields.