This paper attempts to describe and analyze the connection between the unresolved grief of five students at the Academy at Swift River, located in western Massachusetts, and their internationally mobile lifestyles by answering this question: What is the connection between the unresolved grief of five ASR students and their internationally mobile lifestyles? It is answered with regard to familial issues, personal perceptions and identity, and interpersonal behavior. My primary research question is: In order to answer these questions, unstructured interviews were conducted with five Internationally Mobile (IM) adolescents. This primary method of research is supplemented with information about the challenges and benefits of an IM lifestyle as well as the common sources and effects of unresolved grief in other IM adolescents. Two theories frame this analysis: the encapsulated marginal theory of Robert Park and Janet Bennett, and adolescent development theory. The analysis finds that the adolescents share common manifestations of unresolved grief. The adolescents’ emotions and fears are also similar in relation to their family relationships and personal perceptions. In addition, the effects of the adolescents’ IM lifestyles are directly influencing their behavior, communication and social interactions. The distance, disempowerment and instability stemming from their familial relationships are in direct relationship to their unresolved grief. That, coupled with unresolved feelings of loneliness, inferiority and being different, has caused the adolescents to seek protection and acceptance in social situations. My hope in making these connections is to provide information to IM parents and the staff at ASR. Also, the links that the adolescents made during their interview process will assist them with resolution in their lives.