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With the emergence of Artificial Intelligence (AI), all aspects of human-machine interaction have been examined. (Im)politeness has always been a crucial element in all human communications, and it is becoming one of the fundamental components in human-machine interaction. Drawing on well-established linguistic theories of politeness ranging from Robin Lakoff’s politeness rules to Brown and Levinson’s (1979, 1983) concept of face and Leech’s (2014) discussion of (im)politeness strategies and maxims, this chapter aims at analyzing simulations provided by ChatGPT within different personas and contexts to shed light on how AI handles (im)politeness of users’ queries from a linguistic perspective. The chapter opens with an introduction of AI and its applications in different disciplines and the applications of ChatGPT as an AI chatbot. It then proceeds to review different linguistic theories of (im)politeness. It closes by analyzing simulations provided by ChatGPT within different personas and contexts to shed light on how AI handles (im)politeness of users’ queries from a linguistic perspective. The analysis disclosed the fact that ChatGPT, as a model, is trained on responding politely to all users and ignore all kinds of offensive language.