Matchmaker 101

By

Ava Brett

Disclaimer

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

So just in case you missed my Author note last night I have gone back over this story and pretty much rewritten it. I seriously and I do mean seriously recommend that you reread at least chapter six and seven if you haven't already done so because otherwise this chapter eight will make no sense in the context of things.

I felt like I was doing Sam the wrong way in this story so I decided to change it… so that's what I did. I think the story is at least eight thousand words longer then it used to be and I'm a great deal happier with this version so hopefully you will be as well!

Anyway below is the first interaction between Sam and Castiel… I'm sure that Sam had thought it would go so much better in his head… always the way

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 can't tell whether it went well or not…

Overall Romance

Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore

Chapter Romance

We're beginning to stumble towards Cas and Dean…


Chapter Eight

I'm not sure


Sam walked across the room, swerving around the obstacles blocking his way while maintaining a smile on his face for the customers who tried to get his attention. His mind was completely focused on the task at hand as he mentally brushed off Chuck's concerns. What exactly did the older man think he was going to do here? Tell Castiel straight up that Dean fancied him and beg him to ask his brother out so that Dean would be happy and they could all move on?

Sam was a lot of things in this world, both good and bad, but being tactless over issues which required some level of sensitivity wasn't one of his flaws. He had inherited the charisma and charm which every male Winchester seemed to have had designed into their DNA code. The only difference between him and Dean was the fact that Sam was a great deal more particularly about whom he showed it to. Dean was happy to seduce the world at large, making men and women want to be with him. Sam hid it instead, preferring to save it for someone special, someone like Jessica for example.

He licked his lips and breathed in deeply, letting it out slowly as he tried to ignore the fact that he was beginning to feel extremely nervous. This was the guy his brother liked, his brother Dean who rarely showed a romantic interest in anyone because he was always too busy. It was suddenly extremely important to Sam that he made a good impression on the man in front of him. He actually cared for his brother, the last thing he wanted to do was ruin Dean's chances with Castiel because of some jackass move that Sam made.

Setting his shoulders, Sam reached the table, stopping next to it and speaking, making his voice friendly and relaxed.

"It's Castiel right?"

The older man looked up at him at the mention of his name, a flash of annoyance on his face which swiftly turned to surprise when he saw that it was Sam who had disturbed him. There was a moment's silence where they both seemed to measure the other person before Castiel spoke.

"Yes?"

Sam smiled pleasantly at him trying to ignore how awkward the whole situation felt. It had seemed like such a good idea when he had been behind the counter but now that he was actually doing it he wasn't so sure. God he would never hear the end of it if it turned out that Chuck had actually been right and that Sam should have actually listened to him.

Sam quickly glanced behind him at the counter to see Chuck resting both hands on the counter, leaning forward and staring at Sam's head, the minute their eyes met Chuck's expression turned supportive and he waved a hand towards Sam as though he was telling him to get on with it. Sam turned back and spoke.

"Yeah you don't know me and I know how awkward this is but my name is Sam Winchester. I'm erm Dean's brother, I'm hoping that if you've spoken to Dean like you said you have then you might know who I am otherwise this is just plain embarrassing and I'm gonna have to kill my own brother." He remarked, relaxing slightly when a small smile curved Castiel's mouth

"I know who you are Sam Winchester" Castiel answered, lowering the papers he still held in his hand to the table surface and fixing Sam with a thoughtful expression, his eyes moving over his face. "Your brother has mentioned you though I fail to see much family resemblance between the pair of you" Sam latched onto the conversation starter like a man who had been drowning.

"Dean is more like our mum, I kinda look like a mixture" he admitted before he continued to speak. "I guess you must speak to my brother quite a bit then. I haven't really seen you around here before" he probed lightly. Castiel shrugged his shoulder, a slight flush coming across his cheeks as he looked away from Sam for the first time, wrapping his hand around his mug and lifting it to his mouth. He took a sip, setting it back gently on the table before he spoke.

"Your brother is an interesting man to talk to Sam" he remarked casually. Sam nodded his agreement with the assessment.

"That he is, he's always been interesting. I think Dean knows a little something about everything though he tries to make out that he doesn't." Sam confided, surprised by how easy Castiel was to talk to. There was something about the older man which was calming and almost peaceful. As though you could tell him anything and he wouldn't judge you, he would merely listen to the end and then give you the advice you craved. It made Sam want to sit down opposite him, put his feet up on the table and confess everything to him. He wanted to tell him about his never ended work stream, about his desire to be with Jessica and his constant concern for his brother. Instead however he lifted the plate in his hand up.

"This if for you" he stated simply, leaning down and putting the plate on the table. He watched carefully as Castiel looked down at it, a small frown coming to his face before he met Sam's gaze with a puzzled look.

"I didn't order any cake" he said, Sam shrugged his shoulders.

"Oh I know you didn't" he replied offhandedly watching with a sinking feeling as Castiel's puzzled look melted into a frown. He hurried on before the other man could say anything. "It's just Dean mentioned last night how you hadn't tried on the cakes we sell here yet and he mentioned that if I saw you today then I should pick you a cake and give it to you on the house so you could give it a go and know what you've been missing out on."

Castiel's frown disappeared into a look of surprise and warmth as he turned back to look at the lemon tart.

"Dean asked you to bring this to me?" he asked his voice carefully neutral as he reached out and lightly grabbed the plate, dragging it across the table so it was in front of him.

"Yep" Sam said before he grinned widely "You know I don't know if he mentioned it but he actually makes all the cakes and stuff himself. He's always baking trying to keep up because they keep selling out. He's pretty good though I don't tell him that, no one tends to believe me when I tell them, I guess they look at him and decide it's not true"

Castiel looked up at him, picking up the fork Sam had provided him with. Sam could see a look of anger enter the blue eyes at his words which surprised him.

"It doesn't surprise me that Dean made these, he's a talented man" Castiel remarked stiffly, his gaze suddenly hard. "I'll be sure to thank your brother when I next speak to him for his generosity." Castiel tone made it clear that he was dismissing Sam, his gaze moving past him to the door where Dean was "Thank you for bringing me the tart Sam."

"Yeah no problem, I hope you like it Castiel" he remarked, turning and walking back over to the counter with a frown on his face. He actually had no idea how that had gone. Castiel hadn't revealed anything about himself to Sam, if anything it had been the other way round with Sam revealing things to the older man about his brother. Jessica had told him to get some information on Castiel but how was he actually meant to do that when the other man didn't speak about himself.

"Well how did the big epic plan go then?" Chuck demanded the minute Sam was back behind the counter with him. Sam glanced back to the table to see Castiel eating the tart with a look of surprised pleasure on his face.

"I don't actually know" Sam confessed, reaching up and running his hand through his hair as his nibbled at his lower lip thoughtfully. "I haven't done any harm if that's what you're thinking and I did find out that he knows who I am which points to him having more then one conversation with Dean because-"

"Your brother only starts bringing you into conversation from the third time onwards because by then he can tell if the person is worth keeping around." Chuck finished, Sam looked at him with a raised eyebrow, smiling slightly when Chuck went red.

"Oh" Sam remarked.

"What?" Chuck demanded looking embarrassed "Some of us actually pay attention to things which are happening around us" he said huffily, crossing his arms over his chest and turning the subject back to what they had been talking about before. "So did you learn anything else during your stealth mission which you can use in your operation?"

"He thinks Dean is an interesting man" Sam said, rolling his eyes when Chuck snorted.

"Most people do Sam" Chuck said bluntly, tilting his head as he considered Sam thoughtfully. "So what you're actually telling me if that not only did you go over there and find out nothing useful which you didn't know already but you also told Castiel that Dean told you to give him the cake on the house. So let me ask you this wonder boy. What are you going to do when Castiel thanks Dean for the slice of cake and Dean stares back and tell him that he has absolutely no idea what he's talking about. I'm not expert on the workings of Dean Winchester or Castiel's minds but surely the pair of them are going to put two and two together and realise you're scheming."

Sam stared back at him ignoring the sinking feeling in his stomach which Chuck's words produced.

"Err-"he began stopping when Chuck continued clearly on a roll.

"And not only that but what are you going to do when Dean demands an explanation from you because he both know he's gonna, are you going to stare at him like a fish out of water as well?"

"I'll think of something by then" Sam muttered looking away from Chuck and towards the door, thankful for the first time when it opened and admitted the next wave of customers who had clearly just finished in their classes.

He needed to talk to Jessica and he needed to talk to her quickly.

He just hoped that she would know what to do.


Author Note

Next chapter will be up next weekend though I'm not sure what day!

Thanks for reading