Why is it so hard for AI chatbots to talk about race? By researching databases, natural language processing, and machine learning in conjunction with critical, intersectional theories, we investigate the technical and theoretical constructs underpinning the problem space of race and chatbots. We explore how the context of database corpora, the syntactic focus of language processing, and the unadjustable nature of deep learning algorithms cause bots to have difficulty handling race-talk. In each focus area, the tensions of this problem space open up possibilities for creating new technologies, theories, and relationships between people and machines. Through making tangible the abstract and disparate qualities involved in working with race and chatbots, we can pursue possible futures where chatbots are more capable of handling race-talk in its many forms. In this paper, we provide the HCI community with ways to tackle the question, how can chatbots handle racetalk in new and improved ways?