This is unbeta'd so since I'm not American, potentially inaccurate. Sorry if that makes a difference to you. I hope the dates are correct – Sam's supposed to be 18 in his final year because he finishes school a year late.

Summer 1992

Dean was just fiddling with some old car parts, trying to make something of it, when Bobby said, seemingly out of nowhere

"Boy, you oughta think about going to college when you're a bit older."

Dean, not having really been listening grunted, before realising what Bobby had said and looking up.

"What?"

"I'm just saying," said Bobby, "with a mind like that which can build whatchamathingies outa those old things, you could go to college and learn to be an engineer or somethin'. Maybe a mechanic like your dad was."

For the next few days Dean mulled this over, but soon forgot, lost in teaching Sammy how to shoot a gun now he'd got one. So it was a surprise when John mentioned it to him once they'd set up camp at the next motel and sent Sam to get some groceries from the little shop on the corner.

"I hear Bobby's been talking to you," John said. Dean grinned

"You're gonna have to be more specific than that, Dad. I've only been staying there for the past week and a half."

His dad did not smile back "About college, I mean."

"Oh." Dean fumbled for the right thing to say. "Well yeah, he did, but it's not like he was serious or anything. He only mentioned that I could be, um," he spoke his last words softly, rushing over them, "an engineer."

Any hope that Dean may have had was squashed by his father's next words. "Well so long as you know that's no possibility for you, son. You'll make a much better use of your time by staying in the family business – not gallivanting off to college for some far-flung dream. 'Sides, it's safer if we stick together – you, me an' Sammy"

"Yes sir," With a nod of his head, Dean ended the conversation. It wasn't like he didn't want to be a hunter – his dad's job was pretty sweet; why would he want to do anything else?

Fall 2001

It was that memory that surfaced ten years later when Sam was just beginning his senior year.

"Hey, Sammy, what's up?" he asked him in the car. He didn't have to pick Sam up, but since when was Dean Winchester going to skip an opportunity to drive the Impala?

Sam looked at him from the passenger seat, looking both excited and nervous. "So this woman came into school today to talk to us."

"Was she hot?" Dean asked obnoxiously, trying to put his brother at ease.

"Gross dude, she was like, fifty." Dean continued to waggle his eyebrows suggestively so Sam gave up and continued.

"She was explaining about, like, applications. Y'know, for university."

The air was suddenly as bitter for Dean as it had been in that motel when he was 13.

"Well that musta been boring, seeing as you aren't going to college." Dean said, in some sort of mimicry of his father.

Sam scowled. "Who says? Dad? I've wanted this for so long, Dean, I'm eighteen now and I'm not gonna let him stop me doing this!"

Calmly, trying to stop the conversation from escalating, Dean said, "Well you better stop dreaming now Sammy, 'cause I'm telling you, you ain't going to college. What do you even need to go to college for, huh? They don't do degrees in hunting, in case you hadn't noticed."

"Well maybe I don't wanna be a hunter anymore!"

They stopped and stared at each other, Sam breathing heavily. Dean looked confused, Sam furious.

"You know what, forget it. I'm walking home." And so Sam stepped out of the stationary car, slamming the door.

"Sammy-" Dean protested weakly, but it made no difference. Dean was left alone in the Impala to dwell on the argument they'd just had.

"What am I supposed to do now, baby?" he whispered softly.

So this kinda came about from seeing a tumblr post about how Dean could have gone to college to be an engineer, but didn't because he wanted to prtect Sam. IMO, it's pretty unlikely that Dean never thought about it, but I think that he would have shut out any longing he might have had because he valued John's opinion too highly and, unlike Sam, he never really wanted to stop hunting. So yeah, that's where this came from.

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