Disclaimer: Fair-use law is interesting but I don't want to get sued. I own nothing.

Dean would say that his brother was born a geek. He was a breeze to entertain. Just give him a book. Usually, this made him a teacher's dream, too; however, there was an issue with one of Sam's second-grade teachers. Surely an eight-year-old couldn't actually read the Hobbit by himself and do a book report on it? His big brother had responded, "Lady, our dad, works a lot, and I can't stand that elves, dwarves, and dragons crap, so there's no one to read it to him."

Sam's equally geeky determination when researching wasn't a result of his training for hunting. Lots of kids ask why the sky is blue. Only Sam Winchester would, at age 4, be unsatisfied with the vague BS answers Dean made up and then pester Dean and Dad for two weeks straight to be taken to the library to find the real answer. They did eventually agree to take him. They just didn't tell him they were stopping at one place close to the library first.

Sam started screaming the minute he saw the red and white barber pole Sam's long hair didn't start out as a way to piss of his drill sergeant father. The kid had a legitimate phobia of anyone coming near his head with clippers or scissors. You'd think his name was Sam-son. You 'd also think barbers cooked children based on the volume of the screaming and how hard he was fighting as John tried to drag him to the place he feared most in the world. John wondered if he should tell the people now staring at them that they were rehearsing a kidnapping scene for a play.

8-year-old Dean eventually did what he would end up doing eleventy-billion times over the next 19 years, as his younger self would put it. He put an end to the battle between his father and brother. He said, "I told you tricking him wouldn't work. He's still terrified. Just let him keep it long. I'm sure he'll grow out of this weird anti-haircut thing eventually." Years later, as he was practically begging a thirty-something-year-old Sam to let him at least trim his hair, he'd realize his 8-year-old self had been wrong on that last part.