This song always gives me a very specific image: he's performing his songs on stage and a girl who's standing in the crowd grabs his attention. She's in the audience "by the border of the darkness" - that is: as far as the stage lights will reach into the crowd. So he can barely see her, but he caught a glimpse of her "in headlights", probably in between two of his songs when the big lights went on.
He knows he will probably not meet her ("But I'll never find the kid before she's gone"), but he also knows that she'll be somewhere in town ("There's a light on where you're sleeping") and it's almost like he's saying "well, I'm sorry that we never got to meet one another, but I hope that my music helped to cheer you up a little" with his "so I hope somewhere that troubles will be gone".
I could be entirely wrong, and the rest of the lyrics don't really fit this story, but I still like to think this could be the meaning of the first verse and chorus.
This song always gives me a very specific image: he's performing his songs on stage and a girl who's standing in the crowd grabs his attention. She's in the audience "by the border of the darkness" - that is: as far as the stage lights will reach into the crowd. So he can barely see her, but he caught a glimpse of her "in headlights", probably in between two of his songs when the big lights went on. He knows he will probably not meet her ("But I'll never find the kid before she's gone"), but he also knows that she'll be somewhere in town ("There's a light on where you're sleeping") and it's almost like he's saying "well, I'm sorry that we never got to meet one another, but I hope that my music helped to cheer you up a little" with his "so I hope somewhere that troubles will be gone".
I could be entirely wrong, and the rest of the lyrics don't really fit this story, but I still like to think this could be the meaning of the first verse and chorus.