This chapter examines (1) how “awkward moments”—where neither interlocutor takes a turn and both remain silent—are constructed in first-time informal online English as a lingua franca interactional (ELF) interaction, and (2) how these moments are consequential to interpersonal relationships. The data analyzed are part of a Japan–Sweden cultural exchange project where participants signed up for the project as an opportunity for intercultural exchange and the possibility of making foreign friends. Conversation analysis of the initial interaction revealed that a turn-level establishment of empathy does not always lead to the development of interpersonal relationships. How an empathic moment works for the interpersonal relationship depends on whether the participants can endorse their presentations or categorizations of themselves in the category structure embodied in the trajectory of the subsequent talk.