What song reminds you of your first heartbreak?

Loner by Value Pac

There's a blonde haired blue-eyed girl I’d like to know But she won't even give me the time of day I don't know what it is that’s so wrong with me But the ladies just don't look my way So let me think about the reasons there might be Is it 'cause I'm so unattractive? Maybe if I played a sport or made it to the top All the ladies would stand next to me

I never really dated in high school/college. Just didn't really happen until my now wife and I went to coffee for the first time. It wasn't really lack of trying but striking out which is why this song immediately came to mind.

If you want a more serious take lookup The End of an Era by Hopesfall.