For the South Asian reader, especially for the female South Asian reader, the book of Ruth roils with emotions. It stirs up strong feelings on practices and perspectives that are intricately enmeshed within the fabric of Indian society. No other biblical book deals so extensively, and in painful detail, on widowhood. Not many other books present as persistently as Ruth the theme of childlessness. No other book is so enthusiastically prescribed to young Christian women for emulation—prescriptions that seem to be less exegetically faithful and more culturally convenient. We explore these three themes to see if we can read this familiar book in unfamiliar, and perhaps even, subversive ways, so as to better appreciate the Christian faith and challenge ourselves in its practice. Havilah Dharamraj is Head of the Department of Biblical Studies at South Asia Institute of Advanced Christian Studies in Bangalore, India.