To provide a better discussion experience in current argumentative dialogue systems, it is necessary for the user to feel motivated to participate, even if the system already responds appropriately. In this paper, we propose a method that can smoothly introduce argumentative dialogue by inserting an initial discourse, consisting of question-answer pairs concerning personality. The system can induce interest of the users prior to agreement or disagreement during the main discourse. By disclosing their interests, the users will feel familiarity and motivation to further engage in the argumentative dialogue and understand the system’s intent. To verify the effectiveness of a question-answer dialogue inserted before the argument, a subjective experiment was conducted using a text chat interface. The results suggest that inserting the question-answer dialogue enhances familiarity and naturalness. Notably, the results suggest that women more than men regard the dialogue as more natural and the argument as deepened, following an exchange concerning personality.