Matchmaker 101

By

Ava Brett

Disclaimer

None of the characters mentioned it the below work of fiction belong to me in any fashion. I am merely using them for my own entertainment purposes.

Author Note

Here's chapter four.

It was fun writing the dynamic between Chuck and Sam because I wanted to show the prickly friendship between them which was based mainly on snide comments, jokes and lots of teasing. It might not be the healthiest friendship out there but its still a friendship based on the fact that both of them get on with Dean and therefore put up with each other for his sake.

So yep lots of fun!

Enjoy

Overall Summary

For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam if determined he's going to get it.

Chapter Summary

Sam enlists some unwilling help…

Overall Romances

Castiel Novak/ Dean Winchester and Jessica Moore / Sam Winchester

Chapter Romances

Mentions of Castiel / Dean


Chapter Four

Don't make me have to threaten you


Sam entered the coffee shop, his eyes automatically going to the counter to see whether he could see any sign of his brother. It was technically Dean's day off but his brother was known for coming in on those days to try and clear the backlog of small jobs which he had to do, normally making a note of the stock they had and what they needed or the books. Sam had no idea how Dean managed to balance so many figures in his head without the use of a calculator but he wasn't going to complain if it kept his brother occupied and out of his hair for a while.

The shop was surprisingly quiet for once with only a few customers seated at the table either talking to each other or working away on their laptop disregarding the world at large. Other then a few glances his way when he entered everyone seemed intent on ignoring him which was exactly what he wanted for this.

He walked across the room and leaned his body against the counter, resting his forearms against it as he watched Chuck work. The older man was fiddling about with on of the machine against the back wall so he had his back to Sam; a smile of amusement covered Sam's face briefly before he coughed loudly and spoke.

"Hello Chuck"

He grinned when the other man jumped, swearing to himself and barely managing to hold onto the mug which he held in his hand. He turned to face the counter, his blue eyes wide with shock before they narrowed as they focused on Sam's face. Sam couldn't resist raising his hand from the surface and giving the older man a quick wave.

"Jesus Christ Sam" Chucked breathed, glaring at Sam as though he wanted him to explode into flames. "What exactly are you trying to do? Give me a heart attack because you're going the right way about it that's for sure"

Sam lowered his hand again and merely shrugged, plastering a look of innocence on his face as he placed a hand on his chest directly over his heart.

"I'm hurt Chuck that you would accuse me of doing some thing like that to you" he remarked, ignoring the disbelieving snort which escaped Chuck at his words. He leaned across the counter, peering around the coffee machine to make sure that his brother was sitting crossed legged on the floor again doing an inventory. That little move had caught Sam off guard more then once in the past and he was determined that it wouldn't happen again, especially not with the topic Sam was going to bring up.

"Yeah I'm sure your heart is bleeding inside" Chuck remarked bluntly, putting his hand on Sam's shoulder and shoving him back. "Stop sprawling yourself over the counter which I've just spent ages cleaning Sam" he said, Sam rolled his eyes when Chuck continued to speak. "And if you're looking for Dean then you might as well save yourself the effort and stop. Your brother hasn't stepped foot in here today, at least not yet anyway." Chuck amended with a quick glance at the clock.

Sam raised an eyebrow fixing Chuck with a disbelieving look.

"You really expect me to believe that Dean hasn't been in yet?" he demanded "Are you sure that he just didn't come in before your shift and leave before you came?" Chuck shook his head.

"He might have done" Chuck said "But if he did then he must be invisible to escape the notice of both Adam and Charlie. The first thing they told me was that he hadn't been in, I think they were actually worried that he was ill or something" Chuck remarked before looking at Sam. "He isn't ill is he?"

"No he would have got in contact" Sam remarked in concern, ignoring Chuck for a moment as he fished out his phone and checked his messages, he had a few messages from some friends, one from Jessica and none from Dean. Frowning slightly he quickly typed a message to his brother asking if he was okay and pressed the send button. He pushed the mobile back into his jeans pocket before turning round to face the room, looking for anything else out of the ordinary when he saw nothing he turned his attention back to Chuck who was watching him as though he was a bomb which was about to explode into his face. "This works out great actually, I need to you about something and its better if Dean isn't here for it"

Chuck wary look became a full blown worried one, his hands gripping the side of the counter tightly.

"No" Chuck said flatly pushing himself away from the counter and Sam's reach. "Whatever it is that's about to come out of your mouth the answer to it is no, so save your breath and don't even bother asking" Sam watched as the older man crossed his arms across his face with a look torn between determination and sheer terror.

"Come on Chuck, there's no need to be so melodramatic" he stated. "For all you know I could be asking you to lend me a dollar to save the life of a needy child, how bad will you feel knowing you didn't help them?"

"I could survive it I'm sure" Chuck responded as he jabbed his finger in Sam's direction. "The last time I agreed to one of your mental plans Dean almost fired me. Do you know how hard it is to get a job at the moment? Of course you don't you're at Uni still, its almost impossible Sam and even if I did get one the boss isn't gonna be as good as Dean so the answer is no. Thanks for coming to visit but no."

"I think the key word there is almost. He almost fired you but he didn't" Sam said brightly a smile coming back to his face as he thought back to the party he had thrown in the coffee shop without Dean's permission. It had been going fantastic right up until the point that Dean had walked in, he had taken one look around, gritted his teeth and walked out back. Sam winced as he remembered the look in Dean's eyes when he had gone after him to try and explain, Dean had told him to go back outside and then proceeded to ignore Sam for a week. At first Sam had scoffed at the punishment but by the end of a week he had been begging Dean to talk to him again. The silent treatment from his brother was definitely something that Sam didn't want to experience again if he could possibly help it.

"Well that reassure me greatly" Chuck remarked with a shake of his head. "Look Sam if you're going to order something then order it otherwise let me get on with my work. Andy is on his lunch and its just me so I kinda need to crack on before the after lectures rush comes in"

"I'll have a large Vanilla latte with two extra shots of espresso on top" Sam said, looking at Chuck and unleashing his puppy dog look which had never yet failed to get him what he wanted. He was slightly miffed when Chuck merely ignored his look and began preparing his drink for him in a takeaway cup. "Ok enough of the games" Sam said with a sigh. "What if I told you that what I wanted to talk to you about was something for Dean, it's nothing to do with me at all."

Chuck paused in what he was doing and looked up, a suspicious look on his face as he searched Sam's eyes carefully.

"You want to ask me something which will help Dean out?" he repeated, Sam nodded.

"That's right, not me but Dean" Chuck remained silent, clearly mulling over the comment as he finished Sam's drink and passed it over to him, waving Sam's money away when he offered it.

"What exactly do you want to ask me?" he eventually said, picking up a clothe and wiping down the coffee machine, his eyes fixed on the task though Sam knew him well enough by now to know that he was listening to him.

"I want to ask you to watch someone for me, it's nothing sinister and it's not gonna get you fired either before you freak out" Sam said. Chuck looked up at him warily but didn't interrupt instead waiting to hear what else Sam had to say. "We both know that Dean doesn't really have a life outside of this place unless you count his other two jobs" he remarked watching as Chuck acknowledged his comment with a small knowing smile, for an instant Sam watched the older man in confusion before he shook it off "right?" he pressed.

"I wouldn't know" Chuck replied. "Your brother doesn't tend to gossip with anyone, especially not about himself or what he has been up to. Most of the time the most any of us can get out of him is that he's fine and that he had a good evening."

"Yeah that sounds about right" Sam agreed before he sighed, running a hand through his hair "Look as far as I can see Dean likes a guy who comes in here, you've probably served him. He's slightly smaller then Dean, pale, dark crazy hair and blue eyes? Got a really gruff voice like he needs some throat sweets or something ring a bell?" he demanded. Chuck shrugged.

"Maybe, we serve kinda a lot of people in here Sam" he pointed out. "Why do you care about him anyway?"

"Because I want to get him and my brother together."

"Why?" Chuck asked curiously causing Sam to roll his eyes at him.

"Why do you think Chuck? Because I want my brother to be happy" Chuck seemed to consider his words carefully before he spoke.

"Surely if your brother wants to be with the guy then he'll sort it out himself by asking him out. Why do you have to get involved, when that will just complicate matters and make it awkward? You don't even know if your brother or the other guy even like each other" he pointed out.

"Oh they like each other all right, that much is clear. If you think that it's something Dean will deal with himself then you clearly don't know him at all" Sam said pointedly "Dean is much too complex and complicated to ever do something simply. Hence why I'm here"

"Right" Chuck said, tilting his head to once side thoughtfully. "And how exactly am I meant to help you in your one man crusade to interfere in your brother's life?" he asked causing Sam to glare at him.

"All I want you to do is to look out for the guy, his name is Castiel. Watch him and tell me how often he comes in here, whether he comes alone with each other, does he pay attention to Dean, and does he try and talk to him. That's the kind of thing I want to know and for the love of God Chuck do it subtly, I don't want Dean to know what we're doing"

"Right so I'm to spy on the guy your brother likes for you so you can what? Talk to him? Tell him how great your brother is? Because surely he already knows how great Dean is if he's interested in him?" Sam shrugged.

"I haven't decided what I'll do with the information" he remarked.

"And say I was actually mad enough to go through with this plan for you what is in it for me?" Chuck asked simply.

"You'll be helping Dean out, remember him? The boss you actually like?" Chuck eyes narrowed as a slight flush came across his cheekbones.

"Anything else?" Sam leaned over the counter and smiled sweetly at him.

"If you do this then I won't make your life a living hell for the next few months. Think about it no comments, no pranks, I won't embarrass you nothing" he offered.

"And if I say no" Chuck asked. Sam's smile widened.

"Then it will become my sole mission to make your life a living hell for the next few months. There are always ideas floating around my head Chuck just begging to be used on someone." Chuck's eye twitched for a moment before he breathed out noisily and threw his hands into the air in defeat.

"Fine Sam, you win I'll be your watchdog for you but if Dean finds out I'll be telling him that it was all your idea" he said flatly. Sam shrugged.

"You do that Chuck" he said, lifting up his coffee cup and flashing Chuck a smile. "Thanks for my drink by the way, it's almost as good as Dean makes it" he turned and walked towards the door.

Stage one would soon be complete.


Author Note

Four down, three to go… Onwards!

Thanks for reading!