The usage of emoticon has escalated exponentially in recent years, triggered by the proliferation of emoticon design. Yet, our understanding of how emoticon usage and design may interact with each other remains limited. In this study, we undertook an in-depth qualitative approach to elucidate the dynamic process through which emoticon usage and design interact. Highlighting the differences from the conventional IT system design frameworks, we proposed a holistic two-cycle (i.e. rationalism and symbolism) view of emoticon usage and design interactions, and underscored the mechanisms involved.