First off, this is my basic background story for how Sam and Gabriel started out. I think it fits rather well into the series time line and I think it's about time that I put it down so that readers understand how they got together, before Sam ever found out that the trickster was an archangel. Because Sam makes bad choices between seasons 4 and 5. This story also follows seasons 2 to 4 and then the some of 5. I will give the episodes that the chapter pertains to for chronological reasons. The song title pretty much covers the over all plot of their rough start.

(Back to December by Taylor Swift)

(2.15 Tall Tails)

It all started at Crawford Hall when Sam and Dean were checking the professor's office. Sam couldn't lie and say he was physically impressed by the janitor he and Dean met there. He seemed like an average Joe. Although what struck Sam was how the man acted. Normal blue collared workers liked to complain about their jobs, but this janitor was laid back and seemed to enjoy what he did. He seemed to revel in his simple living and carried himself with a confidence that most people did not possess. On top of that, he was charming and slipped in small jokes when he could. Sam, at one point, realized the janitor was flirting with him when he'd laughed in the office; where the professor had taken a nose dive. Sam hoped Dean had been too busy with stuffing his face with chocolate to notice Sam was flustered. The last thing he needed from his brother was that he was being charmed by a man. Sam doubted the gay/girl jokes would ever stop if Dean got a whiff of it.

"Anything else I can do for you boys?" The janitor with no name tag raised his brows curiously.

"Well, I was wondering about why there would be a rumor of a room 669 if there was only 4 floors." Sam answered in the hallway, trying to buy Dean a little more precious time in the room to search for hoodoo. The janitor smiled.

"So, do you always ask about college history or is it your way of small talk?" The janitor rested his hands on his waist, throwing Sam a wink. Sam felt his face warm up.

"Oh, I uh... I guess my small talk is pretty bad." Sam scratched the back of his head.

"Well, shame you came all his way to inspect a room you can't wire up. Are you on the clock?"

"Not really. Actually, we're commissioned. We're here to check out a few places and then we'll head back to the main office."

"Good," The janitor gave Sam a sly grin, "I want to buy you a drink sometime." Sam paused, hearing his heart beat in his ears for a moment. He was being hit on by a janitor.

"Oh, I don't think I'll be in the area for that long." Sam knew not to take up the offer. Even if he'd always been curious. Even if he did find the man a bit charming and attractive. The man hummed thoughtfully.

"That's a shame." He sighed, "If you change your mind, let me know." Sam nodded and before Sam could respond further, Dean returned to his side.

"That's all we need." Dean said and Sam grimaced from embarrassment; Dean stunk of cheap chocolate.

"Sorry about the candy." Sam said and gained a side glare from Dean. The janitor only gave a wide grin and a laugh.

"Nah, it's okay. It's the dead guy's food. I wasn't going to touch it besides throwing it out." The janitor showed them out and Sam held his head.

"You're so embarrassing." Sam groaned as they reached the Impala. He glanced back at the college and saw the janitor waving from the second story window. Sam quickly looked away and got into the passenger seat, hoping Dean took his blush for anger towards Dean's tactlessness rather than his small crush on a shorter man.

The next time he saw the janitor was at the bar, after treating the traumatized frat boy to a few rounds of purple nerples. Dean figured they needed some time to unwind and Sam found himself at the bar, abandoned by his brother for a college brunette.

Sam wasn't feeling particularly like picking up a girl, especially after Dean had quipped "Sam, you need to get laid, so that you can get that stick out of your ass." Dean was already on Sam's nerves for messing with his laptop and it was made worse by his attitude.

The bartender put a beer down in front of Sam and he looked up. The bar was fairly empty and Sam had not ordered a drink. The bartender thumbed down the end of the bar, "That guy bought you the drink."

Sam looked down the bar after the bartender moved on to the next person and Sam realized it was the janitor; still in his uniform no less. The janitor wiggled his fingers at Sam with a flirtatious grin. Sam looked around the bar quickly to make sure Dean had really gone and he gave an awkward lift of his hand in return. It took less than a minute for the other man to slide into the seat next to Sam, drinking what appeared to be a mudslide.

"Stuck around a little longer than you thought?" The janitor grinned at Sam. Sam wet his lips with a sip of beer.

"Yeah. My partner kind of ditched me." Sam admitted shyly.

"Mind some company?" The janitor asked, fingers curled under his chin. Sam glanced quickly at the door. Oh God, he really was being picked up by a janitor, "I told you I'd buy you a drink."

"Yes, thank you." Sam drank from the glass and spun the bottle on the bar top, "I don't even know your name."

"Call me Lee." The janitor had a very infectious smile and Sam started hard at his beer to hide his own from creeping onto his face.

"Sam."

Lee grinned, "So what's a nice cable guy like you doing on a night like this?" Sam took a deep breath.

"Trying not to strangle my partner." After a curious brow was lifted, Sam continued, "He's been an asshole lately."

"Assholes usually just need a taste of their own medicine." Lee tsked.

"Yeah, sometimes." Sam grumbled, sliding lower into his bar stool.

"Hey." Lee tapped Sam's arm, "How about we play darts? You can imagine his face on the board."

"Um, sure." Sam got up and followed the other man to the dart board.

"You wager?" Lee tossed him a wry grin and raised brows, "Keeps the game interesting."

"Like what?" Despite Sam's efforts to play poker faced, he smiled as he set his beer on a near by table.

"Oh, like, if I win." Lee collected the darts from the board and gave him a wistful look, "We go back to my place." Sam scoffed, hiding a smile as he sat in a chair with his beer.

"And what if I win?" Sam asked.

"We could always go back to your place." Lee waggled his eyebrows and Sam grimaced at the idea because his brother was there.

"You're shamelessly trying to get me into bed." Sam muttered.

"Is it working?" Lee stood before him, holding out the color-coordinated darts.

Sam smiled and picked the red striped darts, "Maybe, but I don't want that to be my wager..." Sam could weasel some more info out of the charming janitor if nothing else, "If I win, you tell me all the strange things that have been going on in town."

"You don't look like a gossip queen." Lee smirked.

Sam flushed, "I'm not."

"Pick another. One I don't mind sharing while we play the game." Lee offered.

"If... I win, buy me dinner." Sam finally said and realized how it sounded after it came out. Lee smiled.

"Deal." He agreed, "One game, winner take all."

It only took one game for Sam to realize how much he liked Lee. He was funny and flirty. He did end up indulging Sam with his 6 years at the college and in town. He let slip several of the dirty little secrets; who was sleeping with who, what the frat clubs were up to, what devious influences were around. And they were tied for the last round of darts.

"Sounds like a lot of drama." Sam finally commented. Lee gave Sam another belly tingling grin.

"It is. But hey, as long as they're doing it, I'll continue to be entertained, right?"

Sam's first beer was gone and Lee had moved onto a strawberry daiquiri; and since Dean hadn't shown back up at the bar, Sam indulged himself with a Bloody Mary. The irony was not lost on Sam, but that case hadn't put him off from liking the drink. Sam sat at the table as Lee collected their darts for the last round.

"You're really laid back about everything." Sam observed.

"Not too many reasons not to be." Lee slipped back into his seat with the darts, offering Sam his color, "Good drinks and good company go a long way." Lee sipped from his drink, the fruit was tangible and sweet.

"Yeah, it does." Sam agreed and took his darts, going to the line, "So, you assume you can just win and I'll fall into bed with you?"

"I was more or less working on charming you and you'd swoon. We'd make a good time of it and whether we sleep together is completely up to you." Lee gave him a warm smile.

Sam thought about that as he was throwing his darts and he might have missed the first bullseye because he was mulling over Lee's words too much, but the rest took.

"What about you? Wanting a date? Me thinks I've already got your attention." Lee grinned. Sam was quiet a moment, face flushing with more than the alcohol.

"I've never done anything with a guy before." Sam admitted, "I guess... yeah, I think you're cute."

"Cute? Not studly?" Lee teased and flexed his arms and chest, but it could hardly be seen through the janitor uniform. And Lee was no body builder. Sam laughed behind his hand. Lee gathered his darts and within a few movements, all of his darts were stuck in the center, winning him the game. Sam watched, impressed. It took a lot to beat Sam at darts; a game he practically grew up with, "Well, I guess you have an open opportunity now, don't you?" Lee spread his arms invitingly and Sam felt a bit dumbfounded. Lee lifted a finger, "Only if you're interested." Sam took a deep breath. He'd always been curious and finally, he did have an opportunity with a fairly intriguing man. And Bloody Mary had him thinking; why the hell not? Dean got laid, why not Sam?

"Yeah, I'd like that." Sam finally agreed.