The cultivation of global literacy, a 21st Century Skill, is high up the education agenda of the basic education curriculum practiced around the world today. In 2016, OECD released a document entitled “Global Competency for an Inclusive World”. The definition of Global Competence entails the capacity to analyze intercultural issues critically and from multiple perspectives, as well as to understand how differences affect perceptions, judgments, and ideas of self and others from different backgrounds on the basis of a shared respect for cultural diversity. This study seeks to explore how to design test units assessing 15-year-old students’ knowledge and understanding of intercultural encounters. The title of the test unit is HOLLYWOOD MOVIES. It consists of a number of test items (multiple-choice versus open-ended) to be administered to the examinees on a yet-to-be-designed computer-based testing platform. One issue examined in this test unit is the cultural impact of Hollywood movies in terms of core values transported to the Eastern world. To answer the questions demonstrating higher level of global literacy, students are required to analyze the issues therein critically and from multiple perspectives. Through chatting with the computer agent(s) about the issues on intercultural encounters in a globalized world the researcher understands the perspective that the student takes, at the same time revealing student’s ability to interact with the computer agent(s) respectfully, appropriately and effectively to resolve miscommunications due to differences in perceptions, judgments, and ideas of self and others from different background. Through analyses of the responses to the open-ended questions, progressive levels of student global literacy can be assessed. Upholding the core value of cultural diversity, this study is important to assess student global competence for an inclusive world.