In recent years, the number of international students in Japan has been increasing. These students find understanding indirect expressions challenging while communicating with Japanese people. In this study, we implemented and assessed the impacts of a novel instructional program aimed at teaching social skills in a high-context culture characterized by the frequent use of indirect expressions. We conducted two experiments with students in Japan. Experiment 1 included semi-structured interviews with international students in Japan. Interview analysis revealed that it is difficult to learn to use and understand the intent behind indirect expressions without having first-hand experience communicating with Japanese people who use indirect language, particularly regarding “sassuru”—expressions that allow for multiple interpretations. Experiment 1 highlights the presence of problems that cannot be solved simply by learning Japanese and the challenges of adapting to communication styles characterized by the frequent use of indirect expressions in high-context cultures.Based on Experiment 1, we provided social skills instruction to an experimental group of international students as a teaching intervention. Next, participants in the experimental group and control group (who had not received the social skills instruction) completed questionnaires before and after the experiment. Data analysis verified that the intervention participants (1) developed more awareness of, and interest in, the Japanese culture; (2) became more confident in their interpretation of expressions with multiple meanings and of silence; and (3) became more accepting of ambiguous expressions because they had developed greater understanding. Conversely, the control group participants did not experience similar notable changes.