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This paper describes the parent–child relationships of upper-middle-class Chinese parents and their adolescent children who were “parachuted” to the United States for private high schools. With parents remaining in China and children in the United States, thousands of miles away, such a transnational educational arrangement complicates the already volatile parent–child relationships during the adolescent years. Through ethnographic interviews of 41 students and 33 parents, I demonstrate different forms of child–parent relationships in a transnational education setting: those who found that the further physical and temporal distance has brought the parent–child relationship closer through frequent communications, children who experienced “accelerated growth” yet questioned the necessity, and delicate parent–child relationships due to increasing transnational cross-cultural or intergenerational differences. These types of parent–child relationships are not comprehensive of all the lived experiences of the “parachute generation,” yet they shed new light on transnational education and the unintended emotional dimensions of educational migration. In a transnational context for an economically well-off group, parental absence or separation of children and parents is no longer a clear-cut concept and has different layers of meanings, taking into account the frequency of communication, duration of spring and winter breaks and the existence of third-party agents such as for-profit intermediaries (or educational consultants) and host families. The diverse patterns of parent–child relations reveal the heterogeneity and complexities of “doing family” across geographic spaces and global educational hierarchies, as well as the roles of communication technologies, the tempo of mobilities and educational intermediaries.