[[abstract]]Chinese gen ‘with, and’ has undergone grammaticalization processes and has come to display multi-functional usages, namely, (i) forming part of a nominal compound meaning ‘heel’, (ii) functioning as a verb denoting ‘to follow’, (iii) serving as a preposition marking comitativity, reciprocity, unidirectionality and (iv) serving as a conjunction coordinating two noun phrases at the phrasal level and at the sentential level. This thesis assumes that each of the above-mentioned functions and interpretations of gen is influenced by some semantic as well as syntactic factors. The main purpose of the thesis is thus to establish a “continuum” whereby verbal semantics and the syntactic position of modifying elements interact closely and give rise to the different behaviors of gen. This study shows that (i) at one end of the posited continuum, the behavior of gen is unitary and it always functions as a conjunction, (ii) at the other end, the behavior of gen is complex and it can be analyzed as a verb, a preposition or a conjunction, and (iii) between the two ends, gen can be a preposition and a conjunction. Though the “continuum” notion is the focus of this thesis, a comprehensive study on the syntactic distribution and semantic interpretations of gen as a verb, as a preposition, and as a conjunction is first pursued. Besides, a thorough investigation of the semantic features and thematic roles of the referents that appear adjacent to gen in each function also helps us to establish the continuum model.