A/N: Hey everyone! So, this is my Sam & Dean-centric series of one-shots. The title comes from the Hollies' song 'He Ain't Heavy, He's My Brother.' Each chapter will probably vary length, but this one is a bit short. I hope you all enjoy it nevertheless! The chapters aren't going to be related to each other, unless I specify otherwise.

Disclaimer: Believe it or not, I don't own Supernatural.

Spoilers: None

Omaha, Nebraska

August, 2001

After he and Sam left Truman High School in Fairfax, Indiana, Dean never set foot in a school again – at least not as a student.

It was bizarre, how fluidly the whole thing happened. There was no discussion, no parental interference or outrage, no lecture, no door-slamming or grandiose display of teenage rebellion. He just… stopped going.

Dean had considered dropping out of school for years – they don't teach you how to hunt a werewolf in school, they don't teach you how to do anything he would ever need to know in school. Who cares what the derivative of 2x^2 is when people are dying?

The only reason he had continued to go was because of Sammy. His brother knew how to fight, but he was small and sensitive; anyone who could sense weakness could sense that that little twerp had a bleeding heart. He might as well have had a bull's-eye painted on his back.

Of course, it was Dean's responsibility to protect him, and so he had gone to school – he'd nearly finished school.

But when Dad finished the hunt in Indiana and they moved on to gank a wraith in Phoenix, Sam started up classes and Dean never did. Sam had hit a growth spurt over winter break and didn't really need him anymore, and he was vital and strong and eighteen years old and ready to fully immerse himself in the family business.

Dad agreed.

So, with only one semester of education left to obtain his degree, in typical Dean Winchester-fashion, he quit.

He was never even good at school, anyway. Sammy got the brains, he got the brawn. That's just the way it was. Sure, maybe he was decent at crunching numbers and he was no slob when it came to home ec., but Sam was the one with a real gift. That kid could write. He was going places – everyone could see it. Dean was just his bonafide bodyguard.

Nobody cared that Dean dropped out of high school. Not the teachers, not his own family. No one even mentioned that it happened; it was as natural as the changing seasons, it was expected.

That was fine, though – the monsters didn't care either, so neither did Dean. He already had all the skills he could ever need. Yeah, maybe he was shit with Shakespeare, but he could sure as hell read a roadmap, and the phrases on highway markers were the only ones he would ever need to understand. What could a slip of paper possibly mean to him when his time could be better spent saving people?

Sam was different. Those teachers Dean never gave half a rat's ass about? Sam listened to them. That slip of paper meant a hellova lot to Sam. It meant everything to Sam. It meant more than his own family.

Like he always said – Sam was going places. Sam is going places.

Like right now. Sam's stuffing his shit into an army-surplus duffel bag.

From the doorway, Dean begs, "Sam, please…"

"No," he bites. "No. You know I can't stay here. I can have a life, Dean, a real one."

As though Dean can't. As though none of them ever can except for him. As though this isn't a real life – if it's not real, what is it? Fake? Dean's face must contort in some way, because upon seeing it he amends, "You know what I mean." There's a pause, during which time Sam's indeterminately colored eyes search his. "Come with me," he suggests finally.

Dean blows out a sharp breath from his lungs, turning his eyes up to the water-stained ceiling. "You know I can't," he tells him flatly.

Sam, looking crestfallen, replies, "Yeah. I know."

"Don't go, Sammy," Dean tries again. "Don't go. This family is all we have, all we have ever had."

"I know," he says, laughing bitterly, "I know! That's exactly why I've gotta get out! Can't you see how messed up this is, Dean?"

Of course he can. Of course he fucking can.

But it's not their life that's messed up – it's Sam. He just wants to shake him, shake him until his teeth rattle in his skull and he understands. For someone so smart, he's frustratingly stupid. If there were a Winchester family handbook, it would only have one line written in it: stick together. It's so simple, it's so, so simple. Sam can recognize Iambic Pentameter in a heartbeat. Sam knows what words like 'loquacious' mean. So why the hell doesn't he understand this?

Sam is supposed to know how to read between the lines. He's supposed to understand subtext.

He's supposed to know that when Dad says, If you walk out that door, don't you ever come back, he really means, I love you, son, and I can't lose you too. Please don't go.

If Dean can understand it, Sam sure as hell should.

"Fine. Go," Dean shouts raggedly, beckoning wildly to the ramshackle front door. "Don't let us hold you back any longer."

Sam doesn't understand the subtext in this, either.

A/N: Thanks for reading! Let me know what you think!