Making requests (irai) is a genre of spoken interaction that is taught from the basic level of learning Japanese as a foreign language. A request is one of the speech acts that may raise face-threatening potentials. Understanding the stages of request appropriate to Japanese culture is thus essential for Japanese learners to achieve successful conversation. Therefore, conversation pedagogy by using a discourse approach is essential. This study investigates a potential structure gap in Japanese making-requests conversations realized in actual settings and textbook conversational models. By employing genre theory and interpersonal discourse of “Negotiation” as a qualitative discourse analytic method from the Systemic Functional Linguistics (SFL) perspective, this paper describes the gaps and some factors that potentially influence the structure of Japanese making-request conversation. Data were obtained from conversational texts in the Japanese language corpus named Japanese Natural Conversation Corpus and Japanese textbooks for elementary and middle adult learners. Regarding the structure, the results show no difference between conversations in textbooks and authentic ones at the stage level, but both differ at the phase level. There is no introduction to the problem, additional explanation, and confirmation phases in textbook conversational models. In addition, the absence of the phases, the differences in pre-condition content between textbook and authentic conversations, also the length of the reasoning phase, are assumed to be influenced by relational status between participants (tenor) as well as the imposition degree of the requested object.