This study examines naturally occurring conversations with regard to the syntactic and semantic/pragmatic properties of Japanese quotative particle <i>tte </i>in five different usages and argues that these usages constitute subcategories of the particle <i>tte</i>. Our analysis demonstrates complex and creative uses of <i>tte </i>in contiguity between an object complement marker (OCM) and a sentence-final particle (SFP) as well as between main and subordinate clauses. It also leads to a hypothesis that the SFP usage derives from the OCM usage. This study thus provides an additional piece of evidence for the non-discrete nature of linguistic categories and supports a view of grammar as a temporary outcome of constant change and fluidity in usage, reflecting the dynamic nature of human language.