This study explores learning and meaning-making processes of transnationally mobile youth with ties to Japan (“Japanese third culture kids”) in online tutoring. Based on 2.5-month research from June to August 2020, I utilize a multidimensional, repertoire approach to classroom discourse analysis to investigate how four focal tutee-tutor pairs engage with one another and their learning. Informed by research on after-school educational spaces involving transnationally mobile youth and critical pedagogy, I argue that the tutoring sessions are co-constructed spaces in which interlocutors utilize their communicative repertoires, with emerging themes including mutual acknowledgement of “not knowing” in the L1/L2 and the potential of connection building between learning content and lived experiences. Findings lead to a discussion on the importance of self-reflexive practices, particularly for for-profit educational spaces.