This paper investigates the author's classroom practice of implementing an interpretive perspective on intercultural language teaching and learning in two online intercultural workshops on the topic of face masks designed and delivered during the COVID-19 pandemic. It reflexively examines two critical incidents in classroom practice in terms of what these incidents reveal about the challenges faced by pre-service teachers in operationalizing an interpretive stance towards intercultural language teaching and learning in practice. Based on the epistemology of reflective practice, this self-study seeks to produce knowledge-of-practice by framing the author's practical knowledge as language teacher in relation to theories of intercultural language teaching. Classroom discourse analysis of teaching and learning sequencies provides an emic lens on the enactment of an interpretive perspective on intercultural language teaching at the micro level in terms of two basic aspects of pedagogical practice: 1) Embedding interpretation in learning design and 2) Mediating learners' interpretations in classroom interaction. The findings reveal that this author's attempts to personalise intercultural language learning and elicit meaningful reflections from students were constrained by the limited semiotic richness of the material presented and the difficulty of going beyond a superficial interactional format to provide effective scaffolding and successfully realize a dialogic stance towards knowledge building. The paper considers the implications of these challenges for pre-service teacher education and offers suggestions for supporting teachers hoping to teach interculturally.