Chinese students make up the largest and second largest group of internationals in U.S. and Canadian universities, yet they receive scant attention in terms of how they decide to study transnationally in North America. Most of the research on Chinese families' study abroad decision-making has been conducted with those from first tier eastern coastal cities, while this study includes Chinese families from Lanzhou, Gansu Province, a third tier inland city. This qualitative longitudinal case study explores how Chinese parents and their youth describe the decision-making process; how they understand the challenges and benefits; and how they address the difficulties and opportunities of study abroad. Perspectives and experiences of 11 parent-child dyads in Lanzhou were gathered through individual semi-structured interviews and a focus group interview, commencing before the youth went abroad and concluding after their first year of studies. Data analysis was conducted using NVivo. I discovered that Chinese students and parents made the study abroad decisions in dialectic communication with considerable attention given to developing the youth's capabilities in ways that best fit their own interests, preferences, traits, and talents. While the youth were abroad and experiencing benefits and challenges in the first year, they were seeking the capabilities of developing relational connectedness in cross-cultural contexts and broadening the youth's experiences and perspectives. In their quest, they were challenged by cultural differences, new intercultural competencies, relational and communication paradigms, and academic and intellectual expectations. My study complicates the body of research that largely concludes that Chinese parents make most of the study abroad decisions, and that financial gain, status maintenance, and immigration are the central end goals they seek. It also adds to the body of research that examines the salient challenges and benefits that Chinese students encounter in study abroad in how it shows that these largely revolve around the capabilities they and their families most value. These findings can support those working or studying with North American universities in re-envisioning their understandings of what Chinese students and their families seek in study abroad, and why. Administrators in institutions of higher education, counselors, faculty, and students can find implications for how to better support and work with Chinese students and their families; as well, Chinese families and Chinese international high school divisions can take away insights regarding the decisions, struggles, and benefits in study abroad that Chinese families experience. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]