A magician’s trick and a chatbot conversation have something in common: most of their audiences do not know how they work. Both are also constrained by their own limitations: magicians by the constraints of biology and physics, and dialogue systems by the status of current technology. Magicians and chatbot creators also share a goal: they want to engage their audience. But magicians, unlike the designers of dialogue systems, have centuries of practice in gracefully skirting limitations in order to engage their audience and enhance a sense of awe. In this paper, we look at these practices and identify several key principles of magic and psychology to apply to conversations between chatbots and humans. We formulate a model of communication centered on controlling the user’s attention, expectations, decisions, and memory based on examples from the history of magic. We apply these magic principles to real-world conversations between humans and a social robot and evaluate their effectiveness in a Magical conversation setting compared to a Control conversation that does not incorporate magic principles. We find that human evaluators preferred interactions that incorporated magical principles over interactions that did not. In particular, magical interactions increased 1) the personalization of experience, 2) user engagement, and 3) character likability. Firstly, the magical experience was “personalized.” According to survey results, the magical conversation demonstrated a statistically significant increase in “emotional connection” and “robot familiarity.” Therefore, the personalization of the experience leads to higher levels of perceived impressiveness and emotional connection. Secondly, in the Magical conversation, we find that the human interlocutor is perceived to have statistically-significantly higher engagement levels in four of seven characteristics. Thirdly, participants judged the robot in the magical conversation to have a significantly greater degree of “energeticness,”“humorousness,” and “interestingness.” Finally, evaluation of the conversations with questions intended to measure contribution of the magical principals showed statistically-significant differences for five out of nine principles, indicating a positive contribution of the magical principles to the perceived conversation experience. Overall, our evaluation demonstrates that the psychological principles underlying a magician’s showmanship can be applied to the design of conversational systems to achieve more personalized, engaging, and fun interactions.