The song "Jackson Square" by Mason Jennings tells the story of a couple living in New Orleans, specifically in the Jackson Square area. The lyrics describe the surroundings, such as an old dirt road leading to a graveyard with police cars parked under each light. The narrator reminisces about meeting their partner on Decatur Street, with the person playing the violin while they had their guitar. They quickly fell in love and began a life together, renting a room over Jackson Square. However, things start to change when their partner's behavior becomes strange and distant. The narrator also shares a recurring dream where their partner glows with light and drifts away, which might symbolize their emotional and mental detachment. This dream, alongside their partner's declining mental state, becomes a cause for concern. The song takes a darker turn as the partner's mental health deteriorates further. They begin to hear spirits and receive frightening messages from them, leading to fear and confusion for both the narrator and their partner. The confusion and helplessness of the situation are evident, with the narrator expressing their lack of knowledge about what to do. The song then jumps ahead to a future moment where the narrator wakes up alone and senses something is wrong. Chaos is happening outside, and they discover their partner has disappeared. The imagery of the open window and the weight on their chest adds to the sense of loss and confusion. As the song progresses, it becomes more surreal and metaphorical. The narrator feels old and adrift in an unknown place, observing the universe and thinking of their partner's small presence in Jackson Square. The song hints at the idea of an impending end or conclusion, symbolized by the waiting wings. The lyrics conclude with the narrator struggling to cope, loading a gun while trying to avoid "going there" mentally. The song emphasizes the complexities of life, the lack of clarity, and the struggles faced by the narrator. It suggests that those who claim to understand life fully have never experienced the depths of darkness, mirroring the haunting atmosphere of Jackson Square itself.