The meaning and story of James's song "Dear John" revolves around the end of a romantic relationship. The song portrays the narrator's realization that the relationship has reached its breaking point and they must leave. The lyrics highlight the confusion and entanglement the narrator feels, comparing it to a helix, unsure of where they begin and their partner ends. Despite their efforts to sustain the relationship, they acknowledge that it can no longer grow or be nourished. The song delves into the decision to end the relationship and the fear of expressing this directly to the partner. The narrator sees writing a song as a better alternative to conveying their departure through a letter, text, or email. They believe that speaking face-to-face would be too difficult, so they use music as a medium to express their feelings. The lyrics also reference the significant moment when the couple started their journey together, marked by the year 1999. The mention of synchronized time and a passionate kiss implies that they had a deep connection initially, but now they question if it was all just a ticking time bomb. The song also reflects on the loss of love and the fading allure of intimacy. Every kiss has lost its flavor, and the narrator acknowledges their own behavior and lack of respect in the relationship. They realize that they took their partner for granted and need to rely on more than just friendship to sustain a healthy relationship. Overall, "Dear John" portrays the narrator's decision to leave a deteriorating relationship and their struggle to express this decision. It explores themes of self-reflection, the complexities of love, and the importance of recognizing when a relationship is no longer fulfilling.