Shouldn't Matter But It Does

John Mayer's song 'Shouldn't Matter But It Does' delves deep into the emotional aftermath of a failed relationship, exploring themes of regret, missed opportunities, and the enduring pain of unresolved feelings. The lyrics are a poignant reflection on what could have been, filled with 'shoulda' statements that highlight the singer's introspection and self-reproach. Mayer's use of repetition in phrases like 'Shoulda been open' and 'Shoulda done more' underscores the weight of these regrets, suggesting that the lessons from past mistakes are still haunting him.

The song's chorus, 'Now the road keeps rolling on forever / And the years keep pulling us apart,' paints a vivid picture of time's relentless march and the growing distance between the former lovers. Despite acknowledging that the relationship is over, Mayer admits that the emotional residue remains, encapsulated in the line, 'It shouldn’t matter / Shouldn’t matter, but it does.' This contradiction reveals the complexity of human emotions, where logic and feelings often clash, leaving a lingering sense of what might have been.

Mayer also touches on the idea of mutual responsibility in the breakdown of the relationship. Lines like 'If it’s on someone / Then I blame the both of us' suggest a shared culpability, moving away from a one-sided narrative. The song's raw honesty and vulnerability are characteristic of Mayer's musical style, which often blends introspective lyrics with soulful melodies. 'Shouldn't Matter But It Does' serves as a cathartic expression of lingering pain and the difficulty of moving on, resonating with anyone who has experienced the complexities of love and loss.