He listens, and then says, "I guess I just don't get it."
That's because he's listening to the music, and not the words.
When you can hear a song and feel like the writer has been where you've been, and is echoing what you've felt, it really doesn't matter how the music sounds. It's like you've met that person, because he/she is writing your own feelings.
To me, the words are what matters.
It's the same feeling I get when I'm reading some of Robert Frost's poems.
Or reading certain soliloquies written by Shakespeare. For instance, "Tomorrow and tomorrow and tomorrow.... "
Or even something as simple as Laura Ingalls Wilder's books.
Or the book of Ecclesiastes in the Bible.
I don't think I'm alone in this. Are there songwriters or poets who make you feel as though you know them through their compositions?