This study is about the multifaceted nature of language use in immigrant families. Following earlier explorations of language in the segmented assimilation framework and using adolescent and parental data from the 1995 wave of the Children of Immigrants Longitudinal Study, this article examines how adolescents’ use of English with their parents relates to their proficiency in English and ethnic languages, and their personal language preferences, as well as their parents’ language proficiency and use. The findings suggested that adolescent language choice in child–parent interactions reflected the family’s ways to negotiate the distinct linguistic repertoires of immigrant parents and their children. The adolescent use of English was not necessarily associated with social and emotional estrangement between generations. Even when adolescents generally preferred English, they were less likely to use English in child–parent interactions if their parents, particularly their mothers, were less proficient in English. On the other hand, adolescents were more likely to speak English to their parents if their mothers were proficient in English, regardless of what language parents used with the children. Parents who spoke to their children in English likely responded to their children’s doubts about their ethnic language proficiency and were linguistically and emotionally ready to make that transition.