This study examines naturally occurring conversations with regard to the syntactic and semantic/pragmatic properties of Japanese quotative particle tte in five different usages and argues that these usages constitute subcategories of the particle tte. The analysis demonstrates complex and creative uses of tte 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.