Matchmaker 101


Ava Brett


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

Author Note

Here's the next chapter for you.

I'm sorry for the slight delay in getting this chapter out to you but real life has stepped up a notch at the moment. There's a lot of stuff going on which is keeping me occupied and away from writing so I'm sorry if you've been waiting for this chapter. All I can promise you is the fact that I have no intention of abandoning this story so it most definitely will be finished just as I plan to do the companion story based on Dean and Castiel's views.

I've really enjoyed writing the banter between Luis and Jessica and writing Luis in general is so much fun, I've based him on a friend of mine who actually does act like this. Needless to say I've been embarrassed tons of time in the past!

Anyway please 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 is determined that he's going to get it.

Chapter Summary

He won't stop now, not when they are so close…

Overall Romance

Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore

Chapter Romance

Sam Winchester / Jessica Moore, mentions of Castiel Novak / Dean Winchester

Chapter Ten

Whatever you're doing, stop it!

Sam sighed, glancing around at all the students moving around him, all of them intent on their own tasks. He shoved his hands into the pocket of his heavy winter coat, resisting the urge to check his watch for the fifteenth time in a few minutes, with a great deal of difficulty.

Where the hell was Jess?

Had she changed her mind about meeting him?

Sam had been positive that their date the night before had gone well. They had talked most of the night, almost missing their movie because they had been so involved in a debate over a comment one of their friend's had made about caffeine, it had been a ridiculous conversation to have and yet at the time it had seemed important or maybe it had simply been because she had been getting into it as well. Normally when he tried to start up these sorts of debates with other people they would merely look at him as though he was losing his mind before they would make an excuse and scamper away. Even Dean would sometimes watch him with a raised eyebrow when he went off on one, calling him weird before he went and got them another beer to drink.

When they had eventually parted ways it had been nearly one in the morning and Sam had almost invited her back to his before he had bit down on his tongue hard. The last thing he wanted to do was cheapen the evening no matter how much he might have wanted it. Dean had taught him better then that, if he wanted to win Jessica over and convince her that he was the guy for her then he would have to take it slowly with her instead of rushing head long into things. It was frustrating but he knew that it would be worth it in the end.


Sam glanced up at the sound of his name, a grin coming to his face when he saw Jessica weaving in and out of the crowd heading straight towards him, a matching smile on her face when her eyes met his. She raised her arm above her head and waved at him.

Sam's eyes moved over her face, his smile softening at the sight she made, she looked absolutely freezing, bundled up tightly against the cold, her exposed cheeks and nose red from the sharp, biting wind blowing around them. She looked adorable.

Sam bit back a groan as he shook his head. He must have it bad if he was already thinking like that. Dean would have a field day if he found out.

"Hey Jess" he called back, taking his hand out of his pocket and returning her wave as he took a few steps forward and met her, his smile widening into a grin when she threw her arms around him and hugged him tightly before she stepped back, tilting her head back so she could peer into his face.

"Sorry about that" she stated, looking down from him and glancing around her with a searching look. "You just look so freaking warm that I couldn't resist. I'm sorry I'm late as well; I was just speaking to my Professor after class and time kinda escaped from me. You weren't waiting a long time for me were you?" she asked.

"Five minutes or so" Sam lied with a shrug. "You ready to head over to the coffee shop? I don't know about you but I could just about kill for a Vanilla latte right about now, especially as I know for a fact that Dean is behind that counter today meaning its gonna taste like heaven!" he remarked, raising an eyebrow when Jessica shook her head at his suggestion.

"You can keep your Vanilla latte" she stated. "All I want right about now is a Hazelnut hot chocolate with loads of whip cream squirted on the top of it. In fact the thought of seeing you and having that hot chocolate has been the only thing which has kept me going throughout today, its been a complete and utter nightmare" she said with a sigh, reaching up and tucking some hair behind her ear before she wrapped her arms around her self and squeezed. "Beside we can't go yet Sam, we're still waiting for my friend Luis to appear. He's meeting us today remember?" she asked, glancing up at him with a questioning look. "We spoke about it yesterday before the movie?"

"Yeah I remember the one now" Sam replied resisting the urge to pull Jessica into a hug again. "Luis is the guy you said had a class with Castiel right?"

"That's right" she replied "But I did say that I thought they did. We're not even sure whether Castiel and Professor Novak is the same individual yet. For all we know Sam they could simply be two separate random guys who just happen to work in the same department and share a similar history as each other" she remarked, a twinkle coming to her eyes." Anyway Sam I just wanted to let you know that I had an awesome time last night" she said, her eyes sliding away from his as she nervously licked her lips. "I don't suppose you fancy doing it again some time soon would you?" she asked.

Sam remained silent, waiting until she shot him a quick look before he smiled widely at her.

"What exactly do you have in mind?" he asked. Jessica's shoulders suddenly relaxed as she stood a little taller, a look of relief passing over her features before she shrugged her shoulders at him.

"Well there is this new Italian place which opened up about a month a go or so in the main part of town, I can't remember for the life of me what its called but I do remember that its kinda near your brother's coffee shop maybe a few streets over or something. Anyway I was thinking if you were up for it that we could go out there for dinner one night? Do you even like Italian food?" She asked him curiously.

"Love it" Sam confirmed "Dean went through a stage where all he would cook for us was Italian food, we literally had a new Italian dish every day until he was satisfied that he had perfected them all. If I wanted something more then beans on toast then I had to be his guinea pig" Sam remarked, grinning when Jessica laughed.

"Well the place has been rated highly so I thought we could meet up outside the coffee shop maybe tomorrow at six and head over there and eat" Sam nodded.

"Tomorrow is cool with me" he said "Though it's my treat" he raised an eyebrow when Jessica opened her mouth to argue with him. "Don't even bother Jess, I can be a stubborn git when I want to be and this is one of those times, just ask Dean if you don't believe me, I'm sure he'll love to tell you all about it. God knows he has hundreds of stories about how I ran him ragged when we were younger." He remarked with a laugh as he shook his head. "God knows how the hell he managed it because I doubt I could have" Sam commented, glancing to the side of him with a thoughtful look. He was aware of Jessica watching him for a moment before she spoke, a rare gentle tone to her voice which he hadn't heard before from her.

"Your brother raised you, didn't he Sam" she stated, her tone making it clear that her words weren't a question but rather a statement she was making. "That's why it's so important to you that he's happy. You want to repay him for what he did for you when you were younger." Sam blinked, looking back at her with wide eyes. There was an awkward silence between them, Sam breathed out shakily, cursing him self for speaking so freely in front of Jessica. Their childhood was something that neither he nor Dean spoke of even to each other. They certainly didn't speak about it to others. Sam opened his mouth to say something when another voice spoke.

"Well, well, well Jessica Moore! Aren't you a sight for sore eyes" Sam watched, his mouth falling open slightly when a boy, slightly older then he was, came up to them, throwing his arms around Jessica and lifting her into the air, twirling her round. Sam's eyes narrowed at the sound of her laughter.

"Put me down you idiot before I throw up all over you!" she said, swatting the boy on the arm when he swiftly placed her back on the pavement. She turned to Sam who was watching them and gave him an apologetic look. "Sam this is my friend Luis Sanchez, Luis this is Sam Winchester" she introduced. Luis turned to him, his dark eyes assessing as they moved over him before he suddenly grinned, banishing the serious look from his face as though it had never existed. Sam watched as Luis took a step towards him, his arm outstretched.

"So you're the famous Sam Winchester then" he stated, shaking Sam's hand firmly when Sam's hand curled around his before he released it. "It's great to actually met you in the flesh, our dear Jessica talks about you a lot, to be frank its getting kinda boring, no offence intended towards you of course" Luis remarked breezily. "It's just a relief to know you actually exist and you're not someone who Jess created in an attempt to stop us matchmaking her with men."

Sam glanced towards Jessica, a grin coming to his face when he noticed that she had gone bright red at Luis's words, looking torn between killing Luis with her bare hands or running a mile away from the both of them.

"Well if you've finally finished embarrassing me Luis perhaps we could go to the coffee shop now and see whether the mysterious Castiel and Professor Novak are the same person or not." Luis grinned at her, reaching over and ruffling Jessica's hair with his hand before he threw his arm over her shoulder and began steering her in the direction of the coffee shop.

Sam stared after them for a moment, Jessica hadn't been kidding when she said that Luis was one of a kind.

"Come on Sam" Luis called over his shoulder with an impatient look. "While we're still young would be good." Sam blinked; shaking his head as he hurried after the other two, coming up on Jessica's other side. "So tell me Sam" Luis commented, taking his arm away from Jessica's shoulders and burying his hands into the pocket of his leather jacket, his shoulders hunching up slightly against the wind. "What's your major?"

"I'm studying law" Sam answered back "What?" he demanded suspiciously when Luis suddenly shot him an amused look over the top of Jessica's head.

"You studying law translate into you being a stubborn git who doesn't know when to back down" he remarked lightly with a wink in Sam's direction. Sam stared at him for a moment before he shrugged his shoulders.

"I wouldn't say I was all that stubborn-"he began to say, stopping when Jessica let out an unladylike snort from next to him. She glanced up at him with a mischievous look on her face.

"Oh I'm sorry Sam, I didn't realised you were actually being serious, I thought you were joking" she commented, turning to look at Luis "Sam here is extremely stubborn" she confided "And perhaps the slightest bit deluded if he thinks he isn't" she slipped her arm through his, squeezing his lower arm with her hand to soften her jokey words.

Luis glanced between them, a flicker of understanding coming to his eyes before he shrugged.

"Well that right there might be the pot calling the kettle black" Luis replied "I doubt there's a human being on the face of this planet who is as stubborn as you are once you get going on something Jess" he met Sam's eyes. "Don't let the sweet looking face fool you Sam. She's like a mule, kicks like one as well if you get her pissed off enough" he advised, stepping back quickly to avoid Jessica' foot. "See what I mean, a completely unprovoked attack! Pray tell me what I did to deserve that?"

"Please you know exactly what you did to deserve that" Jessica responded, shaking her head at him. "You're lucky that we need you today or I'd send you home for misbehaving" she commented. Luis held a hand to his chest with an injured look as he shook his head back at her.

"This is what I get for answering your call for help? A ton of abuse?" he stated. "You should be thanking your lucky stars that I'm such a kind and giving person to even accompany you to the coffee shop. Speaking of which by the way we're actually here." Luis commented, stepping in front of them both and opening to the door, moving to the side and making a gesture for them to go into the coffee house first. "After you monsieur and mademoiselle" he remarked innocently.

Sam shot him a suspicious look before he entered the coffee house, his eyes automatically closing as the familiar smell hit them. He opened them slowly, taking a few steps forward so Luis could step in behind them and close the door, blocking out the cold air. Sam rolled his shoulders, felling the tension ease from them as he looked around the crowded shop, his eyes meeting Castiel's almost instantly.

The older man was watching him from the same seat he had been in the last time Sam had seen him with a thoughtful look on his face. Sam watched as Castiel leaned back in his seat, his eyes flickering from Sam to Jessica before they lowered to their linked arms. Sam could have sworn that a look of amusement past over Castiel's features but the expression was gone before he could tell for sure.

Instead Castiel merely nodded his head in Sam's direction in a silent greeting before he looked away from him towards the counter instead. Sam automatically followed the line of his stare, stopping when he met a pair of watchful green eyes. Sam swallowed making him self meet the stare head on. Something was troubling his brother, he could just tell.

"I don't mean to break up your staring competition with the dude behind the counter but your Castiel is definitely Professor Novak" Luis said quietly from just behind him. Sam glanced away from his brother to meet Luis dark eyes over his shoulder.

"You sure about that?" he asked, Luis nodded his head.

"Positive" the other boy replied. "Let me grab myself a drink and then I'll head over there for a word. Jessica said last night over the phone that you wanted to gather some information about him or something similar?" he queried.

Sam nodded his head, glancing back towards Castiel, his eyebrow quirking when he realised that the older man was still staring at his brother. He glanced sharply towards Dean, surprised to see his brother leaning on the counter, his gaze fixed on Castiel. If Sam hadn't of known better then he would have sworn that the pair of them was having a conversation in their minds.

"Lets go and get a drink Sam, I don't know about you but I'm pretty thirsty" Jessica prompted, using her grip on his arm to drag him away from the door and towards the counter. Sam allowed him self to be moved, stopping in front of Dean who turned away from Castiel to look at him. Dean remained silent for a moment, searching Sam's eyes before he turned to Jessica and spoke, a small smile coming to his face.

"Hiya, what can I get you today?"

"We will have a large hazelnut hot chocolate with tons and tons of whip cream on it, a large caramel latte and a large vanilla latte please" Dean nodded.

"Anything else?" he asked.

"You've twisted my arm, I'll have a slice of your lemon tart as well, it's just too damn good to resist" she commented. Dean smirked at her.

"Glad to hear it" he responded "Adam" he called out, turning away from them and looking at the young blond man who was serving drinks to another customer. "Would you mind getting this order for me? I've just gotta speak to Sam in private for a moment."

"Sure thing Dean" Adam replied, flashing them all a smile before he grabbed two large mugs from beneath the counter and started up the coffee machine.

"I've just gotta borrow your boyfriend a moment Jessica" Dean remarked, looking back at them. He met Sam's eyes and jerked his head towards the end of the counter, a look in his eyes which stated that he expected Sam to obey him for once. Sam swallowed, watching Dean walk away before he slowly disentangled his arm from Jessica's, shooting her a reassuring look before he headed over to the end of the counter where Dean was waiting for him with an impatient look.

"What's up?" Sam asked.

"You know the funny thing about raising you Sam if that I know all your little tricks, mainly because I was the idiot who taught them to you in the first place. I always know when you're up to something and I know you're up to something now and I want you to stop whatever it is you're doing" Dean stated, a rare stern note to his voice which was reflected in his brother's eyes.

"I don't know what you're talking about, I'm not up to anything" Sam responded with a shrug.

"Don't play dumb Sam, it doesn't suit you. Cas told me about the cake thing today and how you gave him a piece and told him that I told you to give it to him. If that's not up to something then what the hell is?" Dean demanded. Sam raised an eyebrow.

"It's Cas now is it?" he asked, watching in surprise when Dean suddenly blushed, the red making his freckles stand out.

"Just shut it" the older man stated, looking uncomfortable. "I'll be watching you closely now Sam. I just thought I'd give you a chance to stop now before I'm forced to do something, like embarrass you in front of your new girlfriend, because if anyone can then its me"

"Jess isn't my girlfriend Dean" Sam replied, pulling a face when Dean gave him a disbelieving look.

"Yeah you keep telling yourself that Sam" he remarked, shaking his head before he turned and walked away, leaving Sam staring after him. He glanced back at Castiel, unsurprised to see the older man watching Dean's progress back towards the coffee machine with a look that made Sam shake his head.

There was no way he was going to stop now.

Not when they were so close.

Author Note

Thanks for reading!