As societies become increasingly diverse, there is a corresponding rise in cross-cultural contact, particularly in educational environments. In Japan, international teachers are frequently recruited to teach English to Japanese students, raising questions about the impact of culture distance on this educational encounter. This paper describes a quantitative investigation, which used the Cultural Dimensions of Learning Framework (Parrish & Linder-VanBerschot, 2010) to examine culture distance by comparing the cultural learning preferences of 119 Japanese EFL students and 24 native English-speaking teachers (NESTs) at various universities in Japan. No strong preferences were discovered among either group for preferences categorized as epistemological beliefs or temporal perceptions, while strong preferences were discovered among both groups for preferences categorized as social relationships. Although statistically significant differences were discovered in preferences categorized as social relationships, epistemological beliefs, and temporal perceptions, practical significance was small. These findings both challenge and support depictions of Japanese students and NESTs in academic literature, and suggest a significant number of shared meanings between the two groups in this study. Therefore, the author concludes that the culture distance between these two groups may not be as large as the research suggests, while acknowledging that both groups may have adjusted to each others’ teaching / learning styles. The study illustrates the inherent difficulty in conceptualizing and operationalizing culture distance, particularly through “essentialist” frameworks constructed in a Western context.