Research over the past decades has demonstrated the harmful effects of native speakerism in English language teaching, including how perceptions of native speaker status are deeply intertwined with race and national identity. Recently, scholars have begun to investigate how teacher training programs might push back on native speakerism by providing classroom opportunities for students to challenge their assumptions about native speakers. This article discusses the disruptive potential of an online intercultural learning activity in which MA TESL students in Sri Lanka communicated through digital platforms with undergraduates in New York City. Drawing on data from interviews and students’ online writing, this study suggests that, as students shared videos and “linguistic landscape” images and discussed language differences, the MA TESL students confronted linguistic and racial diversity in the United States, recognizing the presence of dialects like African American Vernacular English and drawing on shared English as a second language status to gain confidence in communicating internationally. Ultimately, both groups of students began to question their beliefs about the superiority of inner circle speakers. The article concludes by discussing the benefits of the increased awareness of linguistic variation, considering how this might encourage teachers to move beyond native speaker standards in the classroom, and offering practical suggestions for implementing similar projects.