Lyric discussion by yesteryear_soon 

this is my take, I don't claim to be an authority on this brilliant songwriter's thoughts.

about the song as a whole: This guy (the character in the song) was with a girl who had depression. He wanted to help her, felt guilty he couldn't make her happy, got angry and they fought a lot. Eventually she ran her car off the side of the road and ended it (suicide). This song is about his emotions dealing with that loss, even long after learning about her death ("many miles since..."). There is frustration and sadness and confusion and rage at different points, but ultimately he can't shake the feeling that he should have been able to "save" her, and at the song he demands of her (or her ghost or her memory:) "How am I supposed to feel?"-- he just doesn't know how to deal with all those intense emotions or how he can ever move on.

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