Through an exploration of Caribbean literature, namely Jamaica Kincaid‟s Annie John and Edwidge Danticat‟s The Farming of Bones, with references to Rosario Ferré‟s The House on the Lagoon and Bartolomé De Las Casas‟ A Short Account of the Destruction of the Indies, I will establish the effects of Western colonization on the Caribbean female during both Western occupation and Western absence. Turning my focus from the Caribbean mother towards her daughter—the progeny of the colonized world—I will then investigate the tenuous binds and boundaries of the mother/daughter relationship, made especially tenuous under the Western gaze. Expanding my view to the modern Caribbean daughter I will examine her ability to define herself, or become, for the first time in many years, “self”—free from both the Western colonizer and her colonizing mother(land).