Master level and optional (Fristående) courses represent a challenge for educators insofar as they gather students from a varied set of disciplines and cultural backgrounds. The challenges range from the students’ home country approach to higher education pedagogy, different disciplinary background, or even different levels of academic accomplishments that go beyond the standardization of academic degrees. Sensitive topics addressed in the humanities, such as questions of gender, sexuality, race, ethnicity, or class, can be particularly challenging when students are encouraged to engage in seminar discussions within a multicultural background. This paper looks at the pedagogic ways in which educators can address these challenges by creating safe environments of discussions that directly engage with the cultural perspective of students while integrating the use of historical sources available in digital archives. The case study is based on a pilot experience conducted during the seminars for the course Moving Images and Gender; a free-standing course in the Film section of the Department of Media Studies. The results of this experience showed that students could attain a degree of distance from the object of study if reflecting upon certain film representations from a historical angle. Allowing the students to present historical examples from their cultures using an analytical/critical perspective helped them reflect upon the discussed topics while developing an emotional distance from the cultural baggage. This approach to seminars reduced the affective response to critical analysis. The students shifted their role from subjects immerse in cultural heritage to cultural mediators, guiding their colleagues into a discovery of cross-cultural perspectives.