Abstract This paper presents a descriptive lexical analysis of spontaneous conversations between users and the 2005 Loebner prize winning chatterbot, Jabberwacky. The study was motivated in part by the suspicion that evidence in support of the Media Equation, especially in the field of conversational agents, was supported by incomplete data; too often omitted in its purview is the occurrence of unsavoury user responses. Our study shows that conversations with Jabberwacky often bring about the expression of negative verbal disinhibition. We discovered that 10% of the total stems in the corpus reflected abusive language, and approximately 11% of the sample addressed hard-core sex. Users were often rude and violated the conversation maxims of manner, quantity, and relevance. Also particularly pronounced in the conversations was a persistent need of the user to define the speakers’ identities (human vs. machine). Users were also curious to understand and test the cognitive capabilities of the chatterbot. Our analysis indicates that the Media Equation may need qualifying, that users treat computers that talk, less as they do people and more as they might treat something not quite an object yet not quite human.