Here's the beginning of an idea: girls who broke my heart, growing up, without having any real culpability.
I've written a lot of songs about girls over the years, many in high school and shortly thereafter, but they were usually about heartbreakers who knew it, who were in it somehow. My first sorta-girlfriend; a good friend who was too flirty for my own meek good; the run up to, duration of, and post-hoc deconstruction of my first serious relationship: I was writing songs saying the things I might have said to them at the time, instead of being too shy to do anything but write a song after the fact.
So here's a song looking at the others—girls I sat back and mooned over, or talked to but never opened up to: crushes and affections not merely unrequited but unrevealed, unperceived. Girls who never had a chance to not break my heart.
Echo of Internet in the blurb about Leeann: "...and who can blame her..."