Abstract: The poem Jiang You Si from the Shao Nan section of The Book of Songs represents a concise yet complex literary work, whose interpretations present significant differences between ancient and contemporary explanation. Various interpretations are based on different understandings of the poem's language and terms. After reinterpreting key terms that significantly influence the interpretation of the poem's meaning, such as "hui" (悔), "chu" (处) and "sighs and songs" (啸也歌), and conducting a detailed analysis of the poem's emotional logic and expressive tendencies, the poem portrays the deep emotional attachment of a woman towards "Zhizi" who is on the brink of marriage, reflecting deep concerns and yearnings of the woman due to her inability to accompany her. The sincere expression of emotions constitutes the charm of this poem. In the Zhou Dynasty society, where the concubine marriage system was prevalent, such concerns and worries conformed to the moral expectations imposed on women within this system. This is the cultural origin of the assertion in Mao Shi Xu that Jiang You Si extols the virtues of the concubine marriage system.