This dissertation involves myself, my two brothers, and our mother embarking, over several years, on a journey to explore the meanings we and others ascribe to our identities as second and third generation Puerto Ricans. Engaging a methodology I dub dialogic ethnography, the study produces a critical interweaving of family history, identity stories, and dialogue, within the context of U.S. racial/ethnic hierarchies. The purpose is to reflect on the ethical implications of our daily performances of cultural assimilation.