This research proposal investigates how cultural differences influence the interpretation and use of emotionally ambiguous emojis in digital communication, with a comparative focus on Japan and China across three distinct age groups. Despite the widespread adoption of emojis as substitutes for non-verbal cues in digital communication, significant gaps exist in understanding how culturally nuanced interpretation of ambiguous emojis operates within East Asian contexts. Current research tends to focus on broad East-West comparisons with limited attention to subtle variations between specific East Asian societies. This study addresses this gap by examining how Hofstede's cultural dimensions interact with generational differences to shape interpretation of ambiguous emojis within the specific contexts of Japanese and Chinese international school communities. Using a mixed-methods approach with stratified sampling of 180 participants (90 from Japan, 90 from China) comprising students (16-18 years) and their parents, this research employs both quantitative surveys measuring interpretation across semantic differential scales and qualitative interviews exploring contextual meaning-making. The findings will clarify how senders' intended meanings diverge from receivers' interpretations across cultural and generational boundaries, providing valuable insights for improving cross-cultural digital communication in our increasingly interconnected world.