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

Holy Moly I've just seen that this story has 122 people following it! That's crazy!

Thank you soooooooo much if you're one of the people who are, it means the world to me.

Just so you know there will be a companion piece to this story which will be done from Dean's perspective. I'll probably start writing it soon but just not yet so look out for it

Sorry for the delay in getting this chapter up, juggling stories and time isn't quite as easy as it used to be but I am trying, updates are probably going to be every two weeks now instead of weekly just so you're aware.

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

Sam makes a bet with Jessica…

Overall Romance

Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore

Chapter Romance

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

Chapter Nine

You are so on!

Jessica shivered in the cold breeze, stamping her feet against the matted snow as she stuffed her gloved hands into her pocket. She glanced around her, eyes lingering on the faces surrounding her as she wondered where the hell Sam was.

They had agreed to meet outside the local cinema at seven so they could catch a seven thirty showing, Jessica has no idea what film Sam had picked for them to view but she didn't particularly care either. She was quite happy to watch anything if it meant spending some alone time with Sam Winchester.

Jessica had liked him from the moment she had seen him across the room at a friend's dorm party in the first week of term. He had been laughing over something, a wide grin over his face his large hazel eyes sparkling in the dim light, his eyes had glanced over to her and she had been lost. He had been surprisingly shy at first though so she had had to work at him slowly, befriending people who were friends with him so she could join their group when they went out drinking or bowling. Slowly she had wormed herself into his life, spending more and more time alone with him in the library, eventually swapping mobile numbers with him and making sure she was available to talk or to see him if he rang or asked her to meet him.

The fact that this situation had arisen with his brother had been the God send she had been looking for to push their friendship up to the next level.

And now, after all her patience and hard work over the last three month he had finally asked her out on a date and he was late. She didn't know whether to be annoyed with him or merely amused.

"Hey Jess, Sorry I'm late" Jessica turned at the sound of her name, a smile coming to her face when she saw Sam jog up to him, a matching smile on his face as he came to a stop by her side. "I was talking to someone and I couldn't get away from them, seriously there are some people out there who can't take a hint!" he commented with a shake of his head.

"That's ok Sam, I literally just got here myself" she lied, "Shall we head inside? I don't know about you but I'm freezing." She commented, Sam nodded his head, a look of guilt coming to his face as he moved, holding the door open for her. "I would have got us the tickets to save time but I wasn't sure exactly which movie you had picked for us to see" she said, looking back over her shoulder at him.

"I'm not bothered by what we see" he answered glancing around them quickly as they walked away from the door and into the warm foyer. "I was thinking we could watch the new thriller which has just been released; I saw when I was checking times out earlier online that there was a showing starting at eight. We could buy the tickets now and then go for a quick drink before hand if you fancied it? Though you know if there was another movie you'd prefer to see then we can see that, I'm easy" he commented, tilting his head to the side with a questioning look on his face.

"The thriller and a drink sound pretty good to me" Jessica answered. "They have a bar here which is kinda nice, I've been here a few time with a few friends and it's always been good up there"

"Cool, well let's grab the tickets first" Sam said, taking his hands from his pockets and rubbing them together. "I've got these" he said when Jessica made a move to get her purse out of the small purse she had brought out with her. Sam placed his hand on her lower back, gently steering her to the small queue in front of the ticket office before he took his hand away, running his hand through his hair with a slight awkward expression on his face. Jessica felt almost sorry for him and decided to take pity on him.

"So you never said how yesterday went. Did you show Chuck what Castiel looked like?" she asked, surprised when Sam's cheeks suddenly flushed pink, an embarrassed look coming across his face as he shifted awkwardly on the spot, nervously stuffing his hands back into his pocket.

"Yeah turns out that Chuck already knew who Castiel was" he said. Jessica waited for more information but Sam remained stubbornly silent, a distant look on his face as though he was caught up in his own thoughts.

"Well that's a good thing isn't it?" she asked cautiously. "I mean if this Chuck guy already knows who Castiel is then it makes life easier, especially if they are on talking terms. He should be able to get some information out of him that we can use. I'm guessing that if the staff know him by name then he's gotta go there quite often, especially when you consider how busy your brother's coffee shop always seem to be" she pointed out. Sam breathed out and nodded his head.

"Yep according to Chuck, Castiel goes in there twice a day, once first thing in the morning and then he goes in there for an hour or so in the late afternoon. He's a professor of Ancient history and classical studies or something along those lines anyway. He's only started this term."

"Holy shit, he's Professor Novak" Jessica stated in surprise. "He's gotta be, it all fits in" Sam turned to look at her, a slight frown on his face,

"You know him?" he asked sounding confused, Jessica shook her head, opening her mouth to speak when Sam held up his hand. "Hold that thought a moment" he commented, sounding distracted as he stepped up to the counter and purchased their tickets from the bored looking cinema worker. He came back to her, placing his hand lightly around her elbow as he steered them both away from the growing queue, letting go of her and passing her over the ticket he had brought her. "We can get some snacks nearer the time if you fancy any" he offered. "Let's get to this bar then, I don't know about you but I could seriously do with an alcoholic drink of some kind."

Jessica nodded her agreement, frowning slightly as she led him up the spiral staircase which led to the bar situated above the cinema. It was fairly busy in there but they were able to buy their drinks and take one of the tables situated by the window giving them a view of the foyer below. Sam waited until she had taken off her coat and was settled before he spoke.

"So Castiel's surname is Novak then?" he asked. Jessica shrugged.

"Well I don't know for certain Sam" she said slowly. "I never made the connection before and I might be wrong but I've got this friend called Luis and he's taking that degree and he told me that they had a new teacher that term, covering someone's maternity leave."

"What does Luis think of him then? Do I know Luis?" he asked. Jessica hid a smile at the barely disguised jealousy in Sam's voice.

"Possibly, you might have seen him at a few of Brady's parties" she commented lightly. "We often hang out together. You should really come out with us one time, I'm sure the pair of you would hit it off straight away. Luis likes Professor Novak" she said, turning the subject back to the important one. "He says he's pretty quiet but he gives an interesting lecture, making the topic come alive which I'm guessing is pretty damn important when it comes to ancient history. Apparently quite a few of the girls in his class have a crush on him though he pays them no attention."

"Yeah, well that part is hardly a surprise is it" Sam said, running his hand through his hair before he reached down and picked up his beer, taking a sip from the glass before he met Jessica's eyes. "I'm thinking that the only person Professor Novak has eyes for at the moment is Dean."

"If Castiel and Professor Novak are the same person then I can speak to Luis and get some more information from him. I'll bring him into the coffee shop tomorrow afternoon. Did Chuck tell you when Castiel tended to come into the shop in the afternoon? Does he have a certain time or is whenever?"

"He said it was nearly always between three and four" Sam answered. Jessica nodded.

"I'm pretty sure Luis mentioned earlier that he was around all day tomorrow because he wanted to meet up in the afternoon. We could meet you in the shop say about two forty five, get ourselves settled at a table and wait for him to come in. Luis can always approach him for us, its not gonna seem weird if one of his own students approaches him while he's out." She stated, frowning slightly when she caught the sudden look of discomfort which came to his face as her words. "What is it?" she demanded.

"I erm… I actually approached Castiel yesterday" Sam said, dropping his gaze to his beer, rubbing his finger pad nervously against the side of the chilled glass. Jessica nodded slowly, ignoring the sudden sense if unease she felt at the way Sam was acting.

"And?" she prompted.

"Well I went up to him with a slice of cake and told him that Dean had mentioned that he had never had a slice of his cake before and that he wanted me to give him a slice if I saw him" he admitted uneasily.

"And did Dean tell you to give him the cake?" she asked, already knowing the answer before Sam had even opened his mouth to reply.

"Erm no" Sam said, pulling a face at his drink before he looked up at her. "It seemed like such a good idea at the time Jess, I thought I could give him the cake because it would give me a reason to start a conversation with him and to find some stuff out about him which he could use, but he got pissed off and kinda sent me on my way."

"Wait, he got pissed off with you and sent you away because you gave his a slice of cake for free?" she asked curiously. Sam shrugged.

"No, not really" he said slowly, a thoughtful look coming to his face. "He seemed pretty damn pleased with the cake especially when I told him that it had come from Dean. He got pissed off when I told him that people never believed that Dean made it. That was when he thanked me for bringing the cake to him. Man I should have actually listened to Chuck for once and just not gone over there. I mean he's gonna go and thank Dean the next time he sees him and Dean isn't gonna know what the hell he's talking about."

"Dean will cover for you I'm sure, he'll tell Castiel that he told you to do it even if its only to save you from looking like a deranged crazy person" she teased. "Beside, what you did shows Dean off in a good light and if Dean likes Castiel as much as you say he does then he's gonna use anything he can to help his case in convincing Castiel to go out with him. When Dean asks you what Castiel was talking about just tell him there was some sort of misunderstanding or something. I doubt Dean will push it, though that's just my opinion, you know him better then I do." She said. Sam nodded looking slightly reassured by her words.

"It was a complete waste of time though" he pointed out with a sigh, "I didn't learn anything at all about him, if anything I ended up telling him about Dean" he stated in disbelief. Jessica smiled, taking a sip of her wine as her eyes moved over Sam's face, he was nibbling on his lower lip and looked adorable.

"I wouldn't say it was a complete waste of time" she commented lightly, meeting his eyes when they moved to her with a questioning expression in them.

"What do you mean?" he asked. Jessica sighed, shaking her head.

"Sam, you've confirmed for us that Castiel definitely likes your brother, that's like one of the most important things which you could have found out from him, more important then finding out what he might like" she said.

"We already knew he liked Dean Jess or we wouldn't be doing this" Sam answered, raising an eyebrow when Jessica shook her head again.

"No we didn't Sam" she said bluntly. "We both assumed that he liked Dean because of the way we saw him acting towards him but we never actually had confirmation that he did. For all we know Castiel could have treated everyone the same way but due to what you found out we known that it isn't Dean is special to Castiel, he likes him.

"Ok rewind" Sam said, holding his hand out looking confused again. "How do you make out that? What makes you think that he's admitted to liking Dean because I was there and there was nothing about the conversation we had which indicated to me that he did!"

"You see Sam" Jessica said flashing him a bright smile. "This right here is the exact reason why I'm here because I pick up on things which you might not have. You said that Castiel sent you on your way after you told him that people had pretty much insulted Dean?"

"Insulted Dean?" Sam replied "Who?"

Jessica rolled her eyes.

"You said that no one believed you when you told them that Dean baked. You know what that says to me? It tells me that what you're really saying is that people look at your brother and the way he looks and don't believe he can do anything which requires some brain power and instead they believe he can only do macho things like fix a car. I mean baking is a hard skill to master, people don't think about it but I'm telling you that being able to bake as well as your brother can is a gift and yes before you ask me, I have eaten your brother's cake, repeatedly on several different occasions because damn they are good cakes."

"Ok I can see where you're coming from and how some people might view it that way but how exactly does that prove that Castiel likes him?" Sam queried.

Jessica briefly closed her eyes, hiding a sigh from the man opposite her. She really hoped he was worth all this effort.

"Think about it Sam, you told him that people didn't believe that Dean was the person who baked the cakes and Castiel took personal offence to it as though you had personally offended him. You don't get pissed off about what other people say about another individual unless you actually have something to do with the individual in question. Now as far as we both know Castiel and Dean only met for the first time earlier this week and Castiel at least, is already protective of your brother. He doesn't want to hear anyone insulting Dean to him, however unintentional it might have been. You were merely relaying information to him which you had been told and he took offence, sending you away even though you were only the messenger. You don't do that unless you care, to be honest though it was a bit of a stupid move on his part. If he's sensible and he does like your brother as much as I think he might do then he's seriously going to be kicking him self over doing it.

"Why?" Sam asked "Not being funny Jess but he wasn't the one who made a complete ass of themselves. Dean is gonna kick my ass when he finds out about it and he's gonna find out soon enough about it because Castiel plans to thank him in person for the cake."

"You'll think of something to tell Dean" she said dismissively before she leaned forward against the table, reaching up and hooking some loose hair behind her ear. "Castiel will be kicking him self because he sent you away." She replied to his first question. Sam breathed out suddenly looking frustrated.

"This whole conversation is making me feel thick" he stated. Jessica laughed at the pout on his face and shrugged.

"Don't worry about it, you are a just a man after all honey" she said with a wink. "Look Sam it's fairly simple when you think about it. Anyone with half a functioning brain knows that you are the most important person in your brother's life, the same way he's possibly the most important in your life at the moment?" she questioned, continuing to speak when Sam nodded at her. "Castiel has just sent the person most important in Dean's life away, in front of witnesses and if that small fact gets back to Dean then he's gonna be pissed because no one gets to treat you that way in his eyes."

"You know that seems a bit farfetched to me Jess" Sam said, wrinkling his nose up. Jessica shrugged again.

"Anything to do with romance and relationship is farfetched Sam" she said. "I mean we've all done crazy things in the name of them both. It wouldn't surprise me in the slightest if Castiel came up to you tomorrow and apologises if he spots you in the coffee shop, especially if Dean is there and watching. Never forget that Castiel wants to make a good impression on Dean and getting you on board with everything which is happening is the best way to do it. If you approve of him then that's half his battle won already because he knows that your opinion matters the most to Dean."

"You seem pretty confident over all of this, fancy making a small bet over it?" Sam asked, Jessica leaned back in her chair feeling intrigued at the sudden change in Sam's manner.

"Depends what the terms of the bet actually are" she answered, watching as Sam slowly smiled at her, resting his hand on the surface of the table.

"If you're right and Castiel does in fact apologise to me tomorrow then I will take you out anywhere you want to go. I'll do whatever you want to do on that day." He stated simply, lightly drumming his fingers against the table.

"Ok and what about if you happen to win and he doesn't apologise to you?" she asked with a smile of her own, her grip tightening on the stem of her wine glass.

"If that's the case then I take you out where I want to go and we do what I want to do with no complaining" Jessica met his eyes, raising an eyebrow.

"Sam Winchester is this your way of asking me out on a date?" she asked playfully. Sam shrugged.

"Do you accept the terms of the bet?" he asked, holding out his hand to her. Jessica glanced down at it before she reached out and grasped it in her own hand, ignoring the butterflies which exploded in her stomach at the simple touch.

"You are so on!"

Author Note

Thanks for reading!