The speaker is looking back on a breakup, or the slow collapse of a close relationship, and struggling to get the memories straight. They think it was about a year ago, probably December, when the two of them were stuck together after school talking about the future. Now that easy hopefulness has turned into something that's falling apart. The speaker admits their memory is bad, yet one detail stays sharp: the boots and jacket the other person always wore.
The tone is casual, awkward, and quietly painful. The speaker keeps apologizing, insists on being honest, and says they'd "die before I lie," but they can't give the other person what they want. The last line is the most striking: "I'm sorry, but I hope you hate me." It suggests the speaker feels guilty enough that being hated would be easier than being forgiven, or that hatred might make a clean break possible. The poem leaves a mood of regret, guilt, and tired honesty.