Exploring the relationship between humans and AI chatbots, as well as the ethical concerns surrounding their use, this paper argues that our relations with chatbots are not solely based on their function as a source of knowledge, but, rather, on the desire for the subject not to know. It is argued that, outside of the very fears and anxieties that underscore our adoption of AI, the desire not to know reveals the potential to embrace the very loss AI avers. Consequently, rather than proposing a knowledge that seeks to disavow loss, we can instead recognize the potential in loss itself: an opportunity to assert and define the gap inherent to both the subject and AI we create.