Disclaimer: I don't own Supernatural in any way, shape, or form

Warnings: Mild language and some (very brief) sexual stuff

The first time Sam asks a girl out…
…he's sixteen and she's seventeen. She's standing with her friends outside of the school, leaned up against the wall. Dean's sitting across the street in the Impala, blasting music. Sam can hear that it's a Motorhead song from across the street, for God's sake.

He can't help but watch her a little bit as he walks down the front steps of the school. She has this straight, long brown hair and these freckles on her nose and these green eyes…

Suddenly, he sees those green eyes connecting with his. Fear clutches in his stomach and he turns away, staring at the ground as he crosses the street. He can hear her giggle trill. God, she even has a cute laugh. He can overlook the giggling for her.

He opens the front passenger door and climbs in, instantly turning the volume of the music down to a level that doesn't deafen him.

Dean turns the music down even lower, which causes Sam to do a double take. Before he can speak, Dean breaks the ice. "Who's the girl?"

"What?"

"I saw you checking her out, she was doing the little," Dean raises his voice to a freakishly high level, "'Ohmigawsh guys he's looking at me, like, cool!'" He laughs as Sam punches him in the shoulder.

"She's not like that."

"Ooh, so we know what she's like now. Fascinating, a little stalkerish for my liking, but all the same - fascinating."

"I don't…I've just talked with her a few times, okay? Nothing major. She's nice."

Dean nods. "Did she give you directions to the library?"

"No!" Sam cries; defensive. Dean gives him the skeptical look that somehow always manages to make him tell the truth. "Okay, yes. But –"

He can't get another word in edgewise because Dean's chortling so loud. He turns up the volume and shakes his head as he pulls out.

The next day Dean's blasting Metallica. "Come on, Sammy," he says as he watches his brother come down the steps of the high school again. He looks at the girl, she looks at him. Woo, a little brave there, sport – he's waving to her now. She smiles, flashing white teeth.

Dean quickly locks all the doors to the car. Sam tries to open the door, and then pulls on it harder. He gives Dean a look, and Dean pretends not to notice because he has the music so loud. Suddenly, he sees Sam starting to pound on the door, and that's not cool. He rolls down the window. "Easy on my baby!"

"Dean, the door's stuck."

"I locked it, Einstein."

"Why?"

"Go ask her out, Sam."

"Now?"

"As good of a time as ever."

"But –"

"Either you ask her our or you walk home, and it's seven miles and they're calling for rain so I don't think you want to do that." He rolls the window back up and shrugs at Sam.

Sam sighs for a second before he mutters "I hate you", turns around, squares his shoulders and marches over to her. He takes her off to the side…Dean smiles as he sees her nodding, reaching into her backpack…oh God, he was getting her number!

Sam comes back over and Dean rolls down the window. "Today," he says, "you finally became a Winchester."

The first time Sam gets his heart broken by a girl…
…he's sixteen, and she's eighteen. (Well, it's the night of her eighteenth birthday, anyway)

They're sitting on a blanket in a nearly deserted park, eating sandwiches. When Sam picks her up, he's afraid that she's not going to go for sitting in the park eating a sandwich with him for her birthday, but he doesn't have enough money to take her to a restaurant. As they pull up to the park, he apologizes for brown-bagging it on their date and she does the little hair twirl thing and kisses him and he remembers how great and cool she is and he knows it's going to be okay.

Then again, he knows that it can't be okay…because he's leaving tomorrow morning, and he's going to tell her on her birthday that they will never see each other again.

Sam always had a flair for timing.

They lie down on the blanket, her pressing into Sam's side and it feels good. "This was really great," she says, and he knows she isn't lying.

"I'm glad you liked it." He smiles. "Happy birthday."

"You know," she says, "this weekend my friend Claire is having a little get-together – very low key, just friends, and I would love it if you could come with me."

Great. "Well, you see…"

She groans and sits up. "Here it comes!" she says. "Another vague reason why you can't come with me somewhere."

"Katie…"

"Don't 'Katie' me!" she snaps. "I'm so sick of this!"

"Look, I'm sorry, but…"

She's sits for a minute, brooding before she turns and looks at him. "Sam," she whispers, "I really, really like you but…" Her eyes cast downward and Sam sits up. His stomach is turning and twisting and exploding all over, and in a second he thinks he's going to throw up.

"Kate," he says, touching her arm, "please…"

She still isn't looking at him and he wants to beg her to look at him, to talk to him, to say something.

She kisses him lightly on the forehead before she whispers, "Goodbye, Sam Winchester." She stands up and walks away.

Sam sits there for a second before he does throw up in the grass.

The first time Sam gets drunk…
…he's sixteen and in a new town. John and Dean are…somewhere, he can't remember where, all he can think about is how much he misses Kate.

He's looking at all of the pictures he has from when they were together, the little trinkets that she gave him and suddenly he's dropping the pictures and things and going into the fridge and the next thing he knows he's on the roof.

He sees Dean and John pull in later, and he waves to them. "Hi!" he shouts, and then he starts to laugh.

John stares up, incredulous. Dean's mouth is in such an 'o' shape he looks like he's about to inhale an egg.

"What the hell are you doing up there, Sam?" John cries.

Sam shrugs and then nearly falls over. "Oops!" he yells and laughs again as he almost falls off the roof, grabbing the loose shingles in an attempt to stay seated.

"Sam, don't move!" John yells. He starts to move when Dean grabs him by the shoulder and says something that Sam can't quite decipher but he doesn't need too, he takes another swig and wow, he really likes beer.

The next thing he knows Dean is up on the roof with him. "Sam," he says, "what are you doing?"

"Oh," Sam says, "you know, just hanging around!" He starts to laugh again and then suddenly he's heaving and Dean's holding his head so he can puke over the edge of the roof.

Sam laughs a little bit more, wiping his mouth. "You know," he said, "the last time I threw up like this we were still in Alton."

"What?"

"Yeah, and it was Kate's birthday and we, you know, we were eating and stuff and all of the sudden she was all mad and…" The words were getting stuck in his throat, and they were raw and hard to say. He clutches the beer bottle tighter. "You know, I really loved Kate."

Dean is still trying to put the pieces together, but he's starting to understand why Sam has been so weird since they moved. He wraps his arm around his brother's shoulder. "Yeah, I know you did, Sam. But hey, there are plenty of other fish in the sea, right?"

Sam looks over at his brother and then punches him in the shoulder…or tries to, he misses by a lot because there are two Deans. "That's funny," he says, as he laughs some more, "because you know I'm allergic to fish!"

The first time Sam walks away…
…he's eighteen and his Dad just said that he'd better stay gone if he's going to go. He pauses for a split second before he goes.

He's made it three blocks before he hears Dean yell, "Sam!" He turns around and sees his brother running, only illuminated by the flickering street light.

Dean finally catches up and he's wheezing from running so fast. "Sam, come on, please don't go like this."

Sam shakes his head. "I'm sorry." He doesn't miss the look of betrayal in Dean's eyes.

Dean opens and closes his mouth, and then runs his hand along the back of his neck. He starts to say something but doesn't finish, and Sam can't catch what he was saying because he's speaking so softly.

"I have to go to the bus stop," Sam says. He starts to walk and Dean follows him. They walk together wordlessly and once they get there they wait wordlessly. They stare at the same spot on the ground for thirteen minutes before the bus pulls up. Sam picks up his bag and starts to get on the bus when Dean says, "Wait!" Sam turns around and Dean seems to be searching for words before he takes a deep breath, shoves his hands in his pockets, and says, "See ya later, Sammy."

The first time Sam sees Jess…
…he's twenty and trying to study for a final. He can't study in his room because his roommate is trying to break up with his girlfriend and she's not taking it very well. It's loud and noisy out here but it works, except for the fact he's being smothered by the joy that's surrounding him – happy college kids who are – yippie! – done with their finals and intent on making enough noise to let the entire state of California know it.

He's hit in the head with a Frisbee and has half a mind to break it when he sees the girl who's coming to get it, and she's really nice enough – he's had a class with her. "Hey Sam!" she says with a smile. "Sorry you got hit, my friend isn't the greatest with aim." She takes the Frisbee. "So, what're you up to?"

"Studying, I still have another final left."

"That sucks. Well hey, if you need a bit of a break you can always come over with us – we found a Frisbee and we're just rekindling a few childhood memories, you know?"

To rekindle any of my childhood memories, you'd have to start laying some salt lines all over campus. "Yeah, I know."

"Chelsea, let's go!" someone yells, and both Sam and Chelsea turn to see a tall blonde girl, arms crossed and tapping her foot. "Waiting here!"

Chelsea takes back the Frisbee and winks before she jogs back to her friends.

Sam can't take his eyes off the blonde girl. He keeps trying to study but gives up as he gaze keeps getting pulled back to her.

Time to call it quits with the schoolwork.

The first time Sam tells Jess he loves her…
…he's twenty-one and lying on the couch, staring at the ceiling. There's a water spot up there that kind of looks like Dean's head, but he can't really trust himself right now, considering he hasn't eaten in about a day and a half and he's still a little woozy.

Jess is sitting on the floor, right by his head. She looks at him; serious. "You really should try to eat something, or drink. You're going to get dehydrated and that's no walk in the park."

Sam smiles a little bit and starts to move but instantly realizes that was a mistake. He bolts up and heads for the bathroom, but there's nothing more to puke up. He makes his way back to the sofa and flops down. "I hate germs."

She gives him a sympathetic look. "Good thing you didn't go for the pre-med thing, then." He appreciates her humor, but if he laughs he thinks he might throw up again. "There isn't anything that you'd want me to go pick up at the store?"

He thinks about it for a second, and then laughs. "Whenever I got sick when I was a kid, my brother would always give me Gatorade, the blue kind. Don't ask me why, but whenever I was sick he'd always come up with a bottle of blue Gatorade and tell me to drink."

Jess is already reaching for her coat and pulling it on. "Then you're getting blue Gatorade!" she says, laughing. She grabs her car keys and starts to kiss him but Sam pulls away.

"I don't want you to get sick too."

She laughs and kisses him on the forehead anyway. "My immune system kicks your immune system's ass. Don't worry about it."

He laughs. "I love you." The words just come out, he doesn't even think about them.

She stops for a second before she says, "I love you too."

A week later, she's lying on the same sofa puking and Sam's offering her blue Gatorade. "I love you," she says, taking a swig, "but I hate your germs."

The first time Sam thinks about going back to his family since he left for Stanford…
…he's twenty-two and in the passenger seat of the Impala. God, he missed this car. Of course, he didn't love it as much as his brother did – no one could love this car in a way like Dean Winchester did – but he always thought it was an awesome car.

They're driving back from finishing off that Constance chick, and Dean's mouth is flying, he can't stop talking and telling Sam about nearly every woman he's banged since Sam left or anything else for that matter. There's a look in his eyes that wasn't there when he first showed up at Stanford...a light that Sam always remembered being there when he was still around.

Sam laughs a little bit as Dean's long-winded recouting of something or other ends, and pulls his neck forward, cracking it a little. He sighs and stares out the window as the world whizzes past.

He remembers the countless hours he spent in this car with his brother, and laughs a little bit as he remembers. "What?" Dean asks.

He turns. "Do you remember when I was like…five, and I hated being in the car?"

Dean snorts. "Do I? You were such a pain in the ass I could never forget it."

"No, it's not that…do you remember that stupid game we'd play so that I'd shut up and not drive Dad crazy by asking, 'Are we almost there?' every few minutes?"

Dean thinks for a moment and then he starts laughing. "The one where the one person would think of something and give three clues and the other person would have to guess what he was thinking about?"

"Yeah, that one!"

"Dude, I love that game so much!"

"'Yeah, I was pretty good at it."

Sam smirks. "That's because I was five and gave way too obvious clues. Had I actually understood that the point was to stump the other person, I would have been so much better."

Dean raises his eyebrows. "Whatever you say, dude."

"Jerk."

"Bitch."

"Asshole."

"Ass...face."

"Ass face? What kind of an insult is that?"

"A good one! It's even more insulting than asshole, in my opinion," Dean says, defensive. "Plus, I get creativity points there, right?"

And for a second, just a split second, Sam misses it. He doesn't miss the hunting or the driving, but he misses Dean and being around him. He forgot how nice it could be sometimes.

But then he remembers and no – he can't go back to this. He has too much to do.

The first time Sam understands how his father felt that night…
…he's twenty-two and in the passenger seat of the Impala, telling Dean to drive as far from Stanford as he can. He's trying to forget it but he can't and every time he closes his eyes he sees her on the ceiling again and there's fire exploding around him.

His clothes still smell like smoke. He can't banish the smell of the smoke from his nostrils. His stomach is churning and bile is rising in his throat.

"Pull over!" he cries, and Dean does. He throws the door open and loses his lunch all over the side of the road. He hears the car door slam and he can feel his brother behind him as he crouches down for a second. His throat burns and his eyes sear.

"Hey," Dean says, "you okay?" Sam doesn't answer. "Come on, there was a motel a few miles back, I'll turn around and we'll call it a night."

Sam nods a little bit and gets back into the car, woozy.

The first time Sam feels alone since he met Jess…
…he's twenty-two and it's three am and he can't sleep but Dean's asleep. He's miles away from Stanford, in…Nebraska? He has no idea. It's worse than trying to keep the days of the week straight.

He slips out of the motel room and sits, leaned up against the Impala. It's cold and he wishes for his jacket, but he doesn't want to go back into the room in case he wakes Dean up so he gazes at the stars, partially obscured by the smog.

And he misses her…he misses Jess. He feels so alone without her, and Sam Winchester hates feeling alone. He wonders if she's up in the stars, staring down at him. He wonders if she misses him this much too, wherever she is.

He hears a door open and close and sees Dean coming out, shrugging into his own jacket. He sits down next to his brother and offers him his jacket.

This is also the last time that Sam Winchester ever feels alone.