We present an exploratory study of how Japanese expatriates adapt to working in the United States over time. We view expatriate adaptation to a host culture through the lens of Experiential Learning Theory and learning style. Results of two studies, using quantitative and qualitative data, conducted in Japanese multinational corporations doing business in the United States reveal how learning style in Japanese expatriates changes over time and how Japanese managers differ from their US counterparts. Results suggested that Japanese managers become more concrete and more active in their learning styles over time spent in the United States, that larger expatriate cohorts are related to slower adaptation, and that language acquisition is related to concrete learning. Results also revealed that the learning style of expatriates changes in response to cultural demands and that the patterns of change do not necessarily reflect that of US managers. We suggest that Japanese managers do not directly assimilate into US culture but develop specialized modes of adaptation to their host culture. Results of the study are generalized into eight propositions to guide future research on expatriate adaptation to a host culture.