Matchmaker 101


Ava Brett


None of the characters mentioned in the below piece of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.

Author Note

Welcome to Matchmaker 101!

This is part one of a two parter story which is mainly done by Sam's and Jessica's point of view. The second part to the story will be done by both Dean's and Castiel, however this has not yet been written as I'd like to finish this story first before I start on the next one.

I try and update as often as I can but it's not always easy to do due to real life getting in the way, however please be patient with me. Matchmaker 101 and the second story will be completed; I have no intention of abandoning either of them.

Anyway please enjoy chapter one


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 is determined that he's going to get it.

Chapter Summary

Sometimes the early bird does catch the worm… Sam just wishes it wasn't quite so early!

Overall Romance

Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore

Chapter Romance

Hints of Castiel Novak/ Dean Winchester though nothing concrete yet.

Chapter One

It's way too early to be out of bed!

"Come on Dean do we actually have to be here today? It's way too early to be out of bed" Sam complained staring at the back of his older brother's head as Dean inserted the key into the lock of the coffee house door and turned it. He turned to look at Sam, a look of amusement on his face which caused Sam to glare at him. It seriously wasn't fair. Dean looked like a stupid ass model that had simply rolled out of bed looking wide awake and perfect while the glance Sam had in the mirror that morning revealed that he looked like an extra for one of the un-dead movies. His skin had been pale, his hazel eyes bloodshot with bags underneath big enough that he could probably have stored shopping in them while his light brown hair had stood up on end looking like he had stuck it in a plug socket during the night and electrocute him self.

He needed a haircut, he needed a shave and he seriously needed to be back in bed sleeping rather then standing in the freezing cold, hands jammed under his armpits while he waited for Dean to hurry the hell up so he could get inside into the warm.

"It's six on a Saturday morning Sammy, it's not like I've dragged you out of bed at three on a Monday morning, I could understand you bitching if I had done that." Dean replied sounding as amused as he looked. Sam rolled his eyes, reaching out and pushing Dean through the door. He quickly shut the door behind him, breathing a sigh of relief as warmth moved over him as he stamped his feet against the mat.

An unwilling smile came to his mouth as he looked around the large room, blinking in the sudden bright light as Dean flicked on the switch by the doorway. Sam had to hand it to his brother; he certainly had built up a place he could be proud of. The room was spacious and clear of clutter while still managing somehow to produce a cosy feel to the room. Squishy dark brown chairs surrounded tables which were spaced with enough room that people could get round them without any problem and could have conversations without worrying about being overheard by anyone. The walls were a light cream colour covered in black and white photos of the surrounding area while the floor was dark brown floorboards.

Sam would never admit it to Dean but the Impala coffee shop had to be one of his favourite places to go.

"You know six in the morning is still freaking early Dean, way too early for anyone to actually be up and thinking about coffee" Sam replied aware that his voice was barely escaping a whine; Dean looked back at him with a raised eyebrow. "You know who is up at six on a Saturday morning Dean?" he demanded, continuing without waiting for an answer "Crazy people, that's who."

"Or maybe just people who have jobs that require them to be up early on a Saturday morning Sam, I can guarantee that they are thinking about coffee right about now, in fact it's probably one of the only things they are thinking about right about now." Dean pointed out as he reached up and dragged the dark grey beanie hat he was wearing off of his head, throwing it onto one of the tables, his gaze moving away from Sam to focus on the large ticking clock behind the counter.

"Yeah crazy people" Sam replied under his breath. Dean turned back to Sam speaking as he began undoing the buttons on his thick winter coat. He looked like the Michelin man, completely bundled up against the cold outside, though somehow the look suited him making Sam hate him for a moment. Dean could wear a bin bag and still look fantastic, it seriously wasn't fair.

"Look Sam, I'm not being funny but you're the one who begged me for some shifts because you needed the extra cash remember. I had to endure a boring ass lecture from you which lasted over a hour about how if I need anything from you then all I had to get off my high horse and ask you blah, blah, blah. I ask you once, just the once to help me open up on a Saturday morning because Anna is sunning it up somewhere on holiday and all you've done from the moment I picked you up this morning is moan and bitch at me about everything. If it bothers you that much then freaking go home, I'll cope alone, it's not like I haven't opened this place up by myself before. Hell I've lost count on the number of times I've done it alone; it's seriously not a big deal."

Sam bit the inside of his cheek, shrugging his shoulders as he pulled his gloves off throwing them on top of Dean's hat on the table surface.

"Okay so maybe just maybe I've been bitching slightly" he admitted, a reluctant smile coming to his face when he caught the disbelieving expression on Dean's face. "Okay you've got me I'm bitching like a spoiled little brat. I'm just tired Dean that's all and I look like a tramp" he whined reaching up and running a hand over his stubble "But cut me a break okay, I was up until three o clock this morning studying for a big ass exam which is next week and when I say big I really mean that it's a really big deal."

Dean frowned back at him as he walked to the counter slipping behind it.

"When you say a big deal Sammy how big a deal do you mean exactly?" his brother asked curiously bending down behind the counter probably checking the state of things. Sam frowned at the question before he shrugged off his jacket, unwinding his scarf from around his neck.

"Well, a third of my grade sort of big deal Dean"

Dean's head suddenly appeared, an exasperated look on his face as he rested his hand on the counter still hunched down, the other hand reaching towards his face so he could pinch the bridge of his nose, his green eyes turning towards the ceiling as though he was asking God for some form of strength so he could deal with Sam without strangling him.

"Then why the hell are you here Sam?" Dean demanded, speaking slowly and clearly. "You should have said something about it sooner to me" Sam watched as Dean stood, pointing a finger to the closed door "Go home and get some sleep because I've gotta be honest with you bro, you look like shit. Get some studying done once you've rested up a bit. I'll be fine here until Jo gets in for her shift later on."

"Yeah but when is Jo due in exactly?" Sam asked suspiciously, his eyes narrowing slightly as he waited for an answer. Dean shrugged.

"Her shift starts at Midday" he answered.

"No way then Dean" Sam replied back bluntly "I was the one who said yes when you asked me to help, it wasn't like I didn't know about the exam. I'm not going to leave you in the lurch dealing with this place by yourself on a Saturday when I know it's gonna be rammed, while I go back and sleep. What kind of a jerk do you think I am that I'd do that to you of all people?" he demanded sounding outraged. "Now get the damn coffee machine on so I can have a cup before the doors open in twenty five minutes admitting the crazy people and this coffee better be on the house Dean or I'll be forced to kick your ass my self."

"I'd like to see you try" Dean said with a laugh as he shook his head "Beside Sammy boy when exactly have I ever charged you for anything in here?" Dean remarked switching on the coffee machines which produced a strangely comforting hum in the air. "Though you know with the sheer amount of my cake you eat I'm beginning to think I should to save you from yourself before you get too fat to move your ass" Sam patted his trim stomach.

"You wouldn't dare" Sam taunted back. "Beside you never have done before. Not once and you don't allow the others to charge me either. In fact the last-"

"Sam I swear to god if you don't stop with this chick flick moment I'm gonna have to kill you and dispose of the body. It's way too early in the morning for this shit. If you want to stay then I'm not gonna say no but if you want to go then I'm not gonna kill you for leaving, you'd just owe me a favour which I can cash in any time I want to in the future and I mean any favour" Dean warned with a smile.

"You're such a jerk!" Sam commented feeling a rare wave of affection towards the older man; He rubbed his hands together glancing around him before he looked back at his distracted brother. "This is normally the bit where you tell me what you need me to do Dean, unless you want me just to stand here and look pretty for the customers when they arrive."

"Yeah you're more likely to scare them off looking like you do at the moment Sam" Dean retorted as he rolled his eyes at him before he began giving him instructions on what he needed to do.

They worked in a comfortable silence, moving around each other and getting things ready for the morning rush, the CD player on filling the coffee shop with the strains of the electric guitar and the beats of the drums. Dean had always listened to classic rock for as long as Sam could remember.

There had been countless mornings which had began in this same way though often Sam had been sitting at one of the tables trying to get some extra studying done before his morning classes. Dean had brought the shop out of the blue when Sam had accepted his offer to attend Stanford University. The boys had moved from Kansas to California with nothing but what they could fit in their car, renting out their old apartment. Why Dean had decided on a coffee shop was beyond Sam but he was certainly glad. The place had been a roaring success from the moment it had opened, attracting the members of the student body into it as well as the countless of other offices and shops which all needed the same shot of caffeine in their veins to start the day.

Sam didn't know how Dean did it, working all day in the coffee shop before heading over to the Roadhouse bar three times a week and working until the early hours of the morning. Hell his brother even did a shift on Sunday at the Bobby Singer's garage. The few times he had asked Dean about why he did it his brother would simply shrug reminding Sam that his scholarship didn't cover everything and therefore they needed the money to survive. Sam wasn't working and therefore as far as Dean was concerned it was his duty as his older brother to support him until he was.

He wondered whether Dean even had a life, did he have friends? Did he go out? Hell did Dean even date anyone because Sam couldn't work out where the time would come from if he did. If Dean wasn't working then he tended to be sleeping trying desperately to keep up with all the demands on his time.

The thought that Dean might be sacrificing his life for Sam made him feel sick to the pit of his stomach.

"Hey!" Sam jumped as Dean's hand clapped down on his shoulder. "Did you hear what I just said to you Sam?" his brother asked, a flicker of concern coming to his eyes. Sam shook his head ignoring the annoyed look which came to Dean's face.

"No what's up?"

Dean jerked his head to the clock.

"It's time to open up sunshine" Dean said slowly. Sam nodded his head, walking to the door and flipping the sign to open; he peered through the glass and shivered at the sight. Snow lay thick on the ground, the sky heavy and dark clearly threatening snow again before the day was through. He should have thought ahead and brought his own car with him that morning but it would have taken too much time to make it ready for the road and the conditions. It had been easier to accept Dean's offer to pick him up on his way.

"Here maybe this will help wake you up a bit" Dean remarked, Sam glanced around as a large mug of coffee was thrust into his hand, he lifted it and smelt it, a grin coming to his face as he recognised the sweet smell of vanilla. His brother knew him too well.

Sam stepped behind the counter just as the door was pushed opened revealing the first cold looking customer of the day. Sam concentrated on taking the orders and getting any cakes of pastries ready, while he watched Dean work from the corner of his eye as the older man swiftly produced the drinks, lightly flirting and chatting with all the customers who clearly adored him if their smiles and familiar banter were anything to go by.

"One tall black Americano with an extra espresso shot please" a gruff voice stated. Sam glanced back to the front of the counter to see a tallish man standing there. He was pale with wild dark hair and bright blue eyes. He looked briefly at Sam before his gaze flickered towards Dean and stopped there as though he was unable to look away. Sam raised an eyebrow as he saw a pink flush cover the man's cheekbones as his mouth fell slightly open. Sam glanced towards Dean unsurprised to see that his brother hadn't even noticed the man or the attention he was receiving from him. For someone who was such a natural flirt Dean was half dense when it came to realising that people were coming onto him.

"Name" Sam asked briskly. The man looked away from Dean with obvious difficulty, a look of embarrassment coming to his face at being caught so obviously staring, his gaze lowered to the counter top.

"Castiel" he answered, Sam nodded.

"Takeaway or are you drinking in today?"

"It's for takeaway thanks"

"Right that will be two dollars fifty then please" Sam stated, ringing it up on the till and taking the five dollar bill from the man, he quickly counted the change out and handed it over to him, pointing down to the end of the counter where two blond students were giggling with each other staring at both Sam and Dean as though they wanted to order them off the menu. Sam grinned; the job certainly had perks at time. "Head over there to collect your order" he remarked. Castiel nodded and headed away from the counter to where Sam had indicated looking around him awkwardly, his eyes lingering on the photos on the wall with a look of interest.

He must have been a new customer because Sam couldn't remember having seen him before. There was no one waiting to be served so Sam turned his attention to Dean ready to chat with his brother once Castiel's drink order was finished, it was the first time since they opened that they had had any sort of break from serving.

"One tall black Americano with an extra shot of espresso for-"Dean turned the cup round "Castiel?" Sam caught his eyes quickly, hiding a grin as he nodded his head towards the man patiently waiting for his drink at the end of the counter.

Dean turned from him, meeting Castiel's eyes for the first time. Sam watched in surprised when Dean's mouth fell open into an O of surprise before he looked quickly away, his hand still held out to Castiel, offering the other man his drink.

Castiel took the coffee, his fingers brushing Dean's as he thanked him. Sam eyebrow rose when Dean blushed at the contact, Dean who never blushed over anything.

"Yeah no problem" Dean muttered. Sam watched as Castiel's serious expression melted into a slight smile, his eyes searching Dean's face before he spoke again.


"Err yeah see ya" Dean answered, his gaze fixed on the older man as he turned and walked away, disappearing out of the door into the darkness outside. For a moment Dean stared after him looking stunned before he shook his head and began to busy himself with cleaning the coffee machine.

Sam grinned.

Now that had been highly interesting.

Author Note

Thanks for taking the time to read!