Author's Note: Hey everyone! First off, thanks to everyone who reviewed "Nemesis". I really appreciate all the kind words, you guys are the best! Here's the next one. It's a shorter entry, so it won't take two decades to get through it lol Kind of a random idea, but a friend of mine told me I should post it. So here it is :) I hope that you like it!

I kinda played around with dates in terms of Sam and Jessica--I have absolutely no idea how or when they met, so I got creative.

Takes place sometime after Scarecrow.

O is for Opportune

Opportune: suitable for a purpose, or occurring at just the right time

He knew that Sam was the emo bitch of the Winchester duo but this was getting stupid.

A week.

An entire week of bitch faces, angst, depressed sighs and one word answers.

It wasn't like Dean needed conversation to keep him entertained. After all, he was perfectly capable of surviving in silence, especially with Sam; they'd never needed to speak in order to have dialogue. It was something they'd worked on and perfected when they were kids, quiet talks in the back of the Impala or in darkened motel rooms when their dad was sound asleep in the next bed.

And it wasn't like Dean was lonely or anything. He could go out and find companionship if he wanted it; they'd passed countless bars on that one highway and there was bound to be…willing members of the fairer sex hanging around.

But meh. He wasn't in the mood.

And that was saying something because he was always in the mood.

They'd finished their most recent case a couple of days before; a werewolf that was stalking a small town in Eastern Alabama—Auburn, to be exact. Right down deep in the buckle of the Bible Belt. Sam had been acting weird throughout the entire job, barely speaking unless he was spoken to and only showing emotion when Dean had been unceremoniously thrown into a tree. He appreciated the brotherly concern, as always, but he was on the verge of losing it. Comfortable silence didn't bother him, but this emo silence? It was starting to get on his damn nerves.

Well, shit.

He really was kinda lonely.

"Hey, I was thinkin'," he started casually, leaning back in the driver's seat. "Why don't we take a couple days? Have some fun or something."

Sam stayed silent for a moment but then spoke in a quiet voice. "Fun?"

"Yeah. Cross a couple state lines and find some good trouble to get into."

"Like you need any help finding trouble."

Dean couldn't tell if the words were said good-naturedly or not but he responded as if they had been. "Come on now, Sammy," he smiled, "you know I always need my wingman."

He watched his baby brother for a few seconds, waiting for some kind of response. He got nothing. Sam just stared ahead, eyes fixed and face completely stoic. Dean returned his gaze to the blacktop and let out a breath, tightening his fingers around the steering wheel.

Ok. That's it.

"You gonna tell me what's going on with you?"

"What do you mean?"

"What do I mean?" Dean glanced over quickly, his eyebrows raised. "I mean this new…quiet, mopey, my dog is dead thing you got goin' on. You've been like this since before Auburn, dude, what's up?"

Catching his lower lip between his teeth for a second, Sam slowly shook his head. His meaning was clear. I'm not talking.

"Sam?"

Sam muttered something that Dean wouldn't have been able to hear even if he was sitting in the kid's lap. He furrowed his brow. "What?"

"I said, it doesn't matter."

"How doesn't it matter?"

"Dean," his voice was low, warning. "Just leave it alone."

And as easily as that, the wall slammed down; a tall, brick, razor-wired son of a bitch that Dean wouldn't be able to climb or knock down. He'd just have to wait until his little brother peered over the top with wide and needy eyes, permitting him entry into all his emotional turbulence. That was a normal routine…Sam's attitude, however, was not.

There were only so many things that could make his usually sensitive and gentle brother so bristly.

Jessica or mom.

He wracked his brain as he tried to remember what the hell the date was. He knew for a fact that it wasn't November 2nd…because if it had been, he would've been in the same boat as his brother.

He would've been worse than his brother.

On the anniversary of their mother, he was always the worst.

That only left Jessica.

Since it wasn't November 2nd, it wasn't the anniversary of the young girl's death that little Sammy was thinking of—even though he mourned her death every minute of every day. No, this was something else. Another day, another memory.

Another landmine for a hapless older brother.

Dean had once bought chocolate chip cookies from a local bakery in an attempt to cheer Sam up. Really bad idea. Chocolate chip had been Jessica's favourite.

Dean had once rented Indiana Jones knowing that Sam liked it and thinking that they could watch it together, like they had when they were kids. Another bad idea. That movie had been Jessica's favourite.

Dean had once found a radio station that seemed to play Staind nearly twenty-four hours a day, Sam's favourite band. And yet another bad idea. It had been Jessica who had introduced him to their emo music in the first place.

Nothin' like a mouth to stick a big ol' foot in, huh?

In the countless months since he and Sam had taken to the road again, he'd been stumbling across things constantly and by accident. Things that seemed to do nothing but break his little brother's heart all over again, which in turn, made Dean's chest hurt. Poor kid.

As if he hadn't had enough of a reason to kill the yellow-eyed bastard.

"This is about Jessica, isn't it?"

Sam said nothing.

Dean sighed quietly. "Look, man…I know what you're goin' through—"

"No, you don't." Sam looked over, his usually benign eyes flashing. "You have no idea."

How old were you when Mom died? Four? Jess died six months ago. How the hell would you know how I feel?

"That's right, because when we lost mom, I was only four…right? What could I possibly remember?"

A truly ugly silence fell in the car and Dean had to fight to keep from completely losing his temper. He knew that he had a short fuse, especially when it came to their mother and the memories of losing her. Because regardless of what Sam thought, he remembered it all—the heat, the smell, the distant sound of her screaming. The memories were as clear at twenty-six years old as they had been at four years old. Time didn't make a difference, to hell with what Sam said or assumed.

Sam seemed to realize the ramifications of what he'd said because he sighed, hesitantly looking over. "I'm sorry, Dean. I didn't…I mean, I don't—" he breathed a bitter laugh. "I shouldn't have said that."

Dean gave a slow nod as if to say 'apology accepted'.

He didn't need to invite Sam to talk again; the kid knew that there was a pair of ears ready and willing if he wanted them or needed them.

After a few minutes where the only sound was the Impala's rumbling engine and the tires cutting through the rain water covering the asphalt, Sam cleared his throat.

Here it comes.

"Today is February 20th."

"Yeah."

"This is the day I first met Jess."

Ah, Sammy.

Swallowing somewhat hard, Dean asked softly, "You wanna talk about it?"

Sam gave a small smile. "You sure you wanna know?"

Dean's aversion to chick flick moments was no secret—hell, he'd rather chew on kitty litter—but when it came to Sam, he was always willing. He may not like it, but he'd do it. Anything for the Sasquatch.

"If you wanna tell me."

When Sam opened his mouth to tell the story, Dean was happy—happy that his brother was sharing something with him, trusting him with it. It was a glimpse into Sam's other life. The life he'd always wanted. Hell, the life he'd deserved.

And something inside began to hurt…

The afternoon sunshine was coming through the high windows with a vengeance and Sam was squinting, straining to read the small print in his textbook. Introduction To Criminal Law. His very freedom, bound and on paper.

His second semester at Stanford University had begun.

He'd been in California for only a few short months, trying to get used to his new found independence. It was bizarre, really, to have so much free time. He could go to the library whenever he wanted, buy his own groceries—fruits, vegetables, bread—listen to his own music, read his favourite books over and over again. He could make friends…make them and keep them. There were no rude wake up calls or ten mile runs at 5:30 in the morning. No sparring or a set amount of time he needed to spend shooting. No races to see who could disassemble, clean, and oil a handgun the fastest.

But as much as he loved it, there was something missing…

There was someone missing.

A big brother.

A best friend.

The guy that had spent nearly forty-eight hours straight teaching him how to tie his shoelaces. The guy that always gave up the last bit of cereal in the box because he knew it was Sam's favourite. The guy that had driven him to the bus depot and given him every dollar he'd saved up from playing poker and hustling pool.

The guy that had leaned against their dad's car and watched, stoically, as the bus had pulled away. No emotion on his face, but a world's worth of emotion in his eyes.

If there was one person in the world that he wanted to share things with—experiences in his classes, with his new friends—it was Dean. He couldn't remember a time in his life when he hadn't shared things with his maverick older brother and the idea of not doing it right then made his breath catch in his throat.

He was finally free, finally on his own, finally doing what he wanted and in charge of his own life.

But he missed Dean.

He let out a breath and dug the heels of his hands into his eyes, trying to relieve some of the sudden pressure—

"Excuse me?"

At the sound of the feminine voice, Sam lowered his hands and turned his gaze upward. There, standing just feet away from him was one of the most beautiful girls he'd ever seen; blonde haired, blue-eyed…fair skin with a splash of freckles across her nose. She was the girl next door. She was the girl Dean would chase after until the end of time if she was willing to put up with him for that long.

He swallowed hard.

"Y-Yeah?"

She smiled radiantly. "I was wondering if you could help me out?"

Sam nodded dumbly. "Sure."

"I'm looking for the Princeton Reviews?" She breathed a small laugh and motioned to the truly enormous library around them. "Do you know what section they're in?"

"Princeton Reviews for what?"

"MCAT testing?"

"You're pre-med?"

The girl nodded shyly. "Yeah, my first year."

"Yeah, me too." Sam motioned to the LSAT prep book sitting on the table in front of him. "I got my Princeton Review yesterday."

Moving a little closer to the table, she peered down at the book curiously. "Law student, huh?"

"Yeah."

"Well, I'll try not to hold it against you."

She winked at him and Sam felt his entire face turn red.

The girl's smile widened.

"Uh, well, uh—" He stood clumsily, nearly knocking over the study lamp on the table in the progress. He reached out to steady it and felt his face get even redder. "I uh, I can show you where they are if you want."

"Great."

"I'm Sam, by the way."

"Nice to meet you, Sam By The Way." She extended her hand and when Sam shook it, he couldn't help but notice how smooth her skin was. "I'm Jess."

Trying not to trip over his own feet, he rounded the table and motioned for her to follow. "Reviews are just down this way."

If only Dean could see me now.

The oldest Winchester brother had only spent years trying to prepare Sam for a world full of girls. Either Dean was a bad teacher or Sam was just too damn shy.

He led her around one of the big oak bookshelves and came to a slow stop about halfway down, pointing up to one of the upper shelves. "The law texts are up there, so," he paused, scanning the lower shelves. "maybe the pre-meds are down here somewhere?"

Jess appeared at his side, remarkably close—so close, in fact, he could smell her hair.

Strawberries.

He wondered if her hair was as soft as it looked…

She all of a sudden had a truly gigantic book in her hands and the skin between her eyes puckered at the sight of it. "Oh my god—" She bit her lip; Sam swooned. "This book is ridiculous."

"Yeah, the uh," He cleared his throat. "The LSAT prep is about the same size."

"And I'm guessing we have to read the entire thing?"

"My Ethics professor said it was a good idea."

She pressed the textbook to her chest and sighed, locking eyes with Sam and sending him another smile. "I guess we both have some serious work to do, huh?"

Sam returned the smile, his bangs falling in his eyes when he shyly looked down to the ground. "Yeah, looks like."

After a second, Jess asked, "What residence are you in?"

"Oak Creek. You?"

"Right around the corner. Wilbur house."

Sam merely nodded.

God, I'm an idiot.

"Well—" She held out her hand again. "Thanks again for the help, Sam By The Way."

He shook her hand and watched as she walked around him, heading towards the end of the aisle. Before he could stop himself, he was calling out to her, "Hey, Jess?" She came to a stop and turned to look at him, her eyes bright and cheerful. Swallowing hard, he said, "Would you maybe…wanna…get lunch or something?" He could feel himself blushing and nearly passed out when she coloured pink as well. "It'd be nice, y'know…getting to know someone."

Jess' blushed deepened and she shyly nodded, clutching her textbook for dear life.

"Yeah. That sounds nice."

Sam swallowed against the sudden tightness in his throat, the tears building in his eyes.

He remembered it so well.

The smell of her hair, the startling color and sparkle in her eyes, the deliciously adorable pink tint to her cheeks...the smell of polished wood and books. It was as if it had just happened, just yesterday, just a second before.

Dean had stayed silent throughout Sam's story but when he finally did speak, his voice was soft and gentle. "Doesn't sound like it took too long for you two to get together."

Sam sniffled quietly and shook his head, letting out a light chuckle. "Nah, we uh," he swallowed. "we didn't start dating until we were sophomores. Until we both moved off campus."

There was quiet music coming from the car's radio, Rolling Stones, and Sam tried to force himself to relax. It wasn't that he was uncomfortable sharing things like that with his brother, not at all…it just hurt. Hurt to think of her, the way she looked, the way she sounded. She'd been perfect. Every inch of her.

Only two weeks after her death, he'd started to panic.

He'd realized that he was forgetting; her laugh, the sound of her voice, the sound of her singing Aretha Franklin in the shower at ungodly hours of the morning. For two years that had been the soundtrack to his life; just as Metallica, the rumble of the Impala and his brother's voice had been the soundtrack before Stanford.

"She was beautiful, Sam."

Dean's voice drifted across to the passenger seat and it was as sincere and kind as Sam had ever heard it.

When he'd first met Jessica, it had surprised him how similar she was to his older brother. They'd had a lot in common—a love of hard rock, muscle cars, leather and homemade apple pie. Throughout those four years of knowing her, having her in his life, it had crossed his mind probably a thousand times that were Jess and Dean ever to meet and actually spend time together, quality time, they would've probably gotten along.

After Dean got passed the obnoxious flirtation stage, anyway.

It had always been a hope of his to one day introduce his brother to the girl of his dreams. To maybe have them be friends, family even. To have all the people he loved together in one room, even if it was for a short time.

But at that moment, all Sam could do was nod, feeling the burn in his throat again.

"Yeah," he responded quietly. "She was."

END