For a number of historical symbols, their signifieds on the connotative level were formed in particular historical contexts, and they effectively reflect the evolution and development of the Chinese society at different stages of history. This chapter examines some of the best-known cases in an effort to unveil the mysteries of how typical Chinese symbols are communicated. The evolution of different signifieds is what we call the semantic multiplicity of the signified. A symbol's signified on the connotative level is developed in particular historical contexts, as a result of the second interpretation of meaning located on the denotative level. It is produced in the specific cultural space where a symbol is applied, that is, the symbol's unique historical context. The process of constructing connotative significations is a process of man-made selections and interpretations, a process which is extremely covert and implicit because it seems extremely natural.