This chapter examines the long-term impacts of nearly 50 years of US study abroad in Japan by mapping the individual outcomes through a transnational lens. The mixed-method study identified the study abroad experience as a pivotal experience influencing participants' subsequent academic, career, and personal development. The potential of Japan Study to influence individuals' life trajectories over five decades lies in the study abroad program's design that provides guidance and opportunities for immersion into the host society and culture. Participants develop a lifelong connection to the host country Japan. They also gain an awareness and connection with the host region of Asia and the wider world in their subsequent life paths. The polarization effect of the study abroad experience has the possibility to result in lifelong affinity or disengagement with the host country depending on how participants navigate new sociocultural terrains during their study abroad experience. Although study abroad is one way to foster future US-Japan connectivity, the mixed findings suggest that the issue is much more complex and goes beyond the acclimation of individuals to the language, culture, and society of Japan during their undergraduate study abroad experience.