As schools in English-speaking countries become increasingly diverse, there are new and increasing opportunities for students to engage in intercultural conversations. Although such conversations have the potential to enrich the learning experience of all in the classroom, difficulties of understanding are likely to arise. The challenge is to pre-empt, identify, and collaborate to negotiate such difficulties. Proficient speakers of English and English-language learners alike then have need of dispositions to, knowledge about, and skill in intercultural conversation. This article suggests some ways of equipping both groups of students with resources for managing intercultural conversations productively in the new linguistic worlds of 21st-century classrooms. The focus is on preparing students for both literal participation in conversation and engagement with the ideas and experiences of others.