This chapter reports findings from a six-week-long asynchronous online discussion forum between intermediate-level Hindi language learners in the United States and English language learners in India, where participants analyzed a Bollywood film and discussed themes related to language ideologies and cultural identities in Hindi and English. Using Cultural-Historical Activity Theory (CHAT), the study conceptualized the given cultural exchange as an activity system, examined the different components of the system (subject, mediational tools, rules, community, division of labor, and object) and highlighted the contradictions and outcomes that emerged within the system. The analysis revealed that the online activity system was dynamic and multilayered, where each component played an important role in how nationalist and traditional concepts of language, culture, and identity were reinforced, challenged, and renegotiated by the participants. Additionally, the results showed that technological, affective, and academic contradictions altered the dynamics of the system and limited participants’ opportunities for learning. The chapter provides pedagogical implications highlighting the critical importance of centering language learners’ diverse linguistic practices and cultural references and prior technological experiences when seeking to develop their transcultural competence in an online context.