“美麗” and “漂亮” are a pair of commonly used synonyms in the modern Chinese language. It is difficult to distinguish between their semantics and the linguistic feeling. Their similarity in semantics may cause great confusion to people coming from another culture; since they do not have the benefit of the same lexical intuition as a native speaker. By investigating the relationship between semantics, grammatical rules and lexical structures, and by studying many situations where the two words are used, this essay tries to find out the proper usage of “美麗” and “漂亮”. Three criteria are proposed to determine their differences -- continuity, change-of-state and control. After knowing their semantic differences and understanding the origins, we might be able to establish similar rules for other synonyms in Chinese.