This is a hauntingly beautiful song about introspection, specifically about looking back at a relationship that started bad and ended so poorly, that the narrator wants to go back to the very beginning and tell himself to not even travel down that road. I believe that the relationship started poorly because of the lines:
"Take me back to the night we met:When the night was full of terrors: And your eyes were filled with tears: When you had not touched me yet"
So, the first night was not a great start, but the narrator pursued the relationship and eventually both overcame the rough start to fall in love with each other:
"I had all and then most of you"
Like many relationships that turn sour, it was not a quick decline, but a gradual one where the narrator and their partner fall out of love and gradually grow apart
"Some and now none of you"
Losing someone who was once everything in your world, who you could confide in, tell your secrets to, share all the most intimate parts of your life, to being strangers with that person is probably one of the most painful experiences a person can go through. So Painful, the narrator wants to go back in time and tell himself to not even pursue the relationship.
This was the perfect song for "13 Reasons Why"
Staring out of his window as the world rushes by
Arthur Robinson closes the glass and replies,
"I dream of Ballerinas and I don't know why
but I see Cadillac's sailing
I was born on the shores of the Chesapeake Bay
But Maryland and Virginia have faded away
And I keep thinking tomorrow is coming today
So I am endlessly waiting
And the comet is coming between
Me and the girl who could make it all clean
Out there in the shadow of the modern machine
Walks St. Robinson in his Cadillac dream.
Carrie's down in her basement all toe shoes and twinned
With the girl in the mirror who spins when she spins
From where you think you'll end up to the state that you're in
Your reflection approaches and then recedes again
And the comet is coming between
Me and the girl who could make it all clean
Out there in the shadow of the modern machine
Walks St. Robinson in his Cadillac dream.
I have dreamed of a black car that shimmers and drives
Down the length of the evening to the carnival side
In a house where regret is a carousel ride
We are spinning and spinning and spinning and now...
There's a hole in the ceiling down through which I fell
There's a girl in a basement coming out of her shell
And there are people who will say that they knew me so well'
I may not go to heaven
I hope you go to hell
And the comet is coming between
Me and the girl who could make it all clean
Out there in the shadow of the modern machine
Walks St. Robinson in his Cadillac dream.
Arthur Robinson closes the glass and replies,
"I dream of Ballerinas and I don't know why
but I see Cadillac's sailing
I was born on the shores of the Chesapeake Bay
But Maryland and Virginia have faded away
And I keep thinking tomorrow is coming today
So I am endlessly waiting
And the comet is coming between
Me and the girl who could make it all clean
Out there in the shadow of the modern machine
Walks St. Robinson in his Cadillac dream.
Carrie's down in her basement all toe shoes and twinned
With the girl in the mirror who spins when she spins
From where you think you'll end up to the state that you're in
Your reflection approaches and then recedes again
And the comet is coming between
Me and the girl who could make it all clean
Out there in the shadow of the modern machine
Walks St. Robinson in his Cadillac dream.
I have dreamed of a black car that shimmers and drives
Down the length of the evening to the carnival side
In a house where regret is a carousel ride
We are spinning and spinning and spinning and now...
There's a hole in the ceiling down through which I fell
There's a girl in a basement coming out of her shell
And there are people who will say that they knew me so well'
I may not go to heaven
I hope you go to hell
And the comet is coming between
Me and the girl who could make it all clean
Out there in the shadow of the modern machine
Walks St. Robinson in his Cadillac dream.
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I think your first comment is closer to being accurate. The singer/song writers state "Millions of eyes can see, yet why am i so blind!? When the someone else is me, its unkind its unkind". I believe hes referring to the girl toying with him and using him. He wants something deeper with her, thats why he allows himself to be as a puppet (even though for her fun and games) as long as it makes her happy. But he knows deep down that she doesnt really want to be serious with him and thats what makes him.
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"In a house where regret is a carousel ride We are spinning and spinning and spinning and now..."
That line is absolutely poetic. I, myself, see it as a family who's messed up, and do things that they wish they hadn't done, because they affected their loved ones by doing it.
At least, that's what I think of, seeing as I can relate.