AN: So, I've sat up all night and morning to get this finished for you all! Thank you all so far for all the kind words, you guys seriously rock! This chapter is dedicated to 101FrozenFire101 as a [belated] birthday present (:
Don't forget to review, it makes me happy to see what you guys have to say!


Dean collapsed down on his bed, sighing loudly. Sam looked up from his laptop curiously.

"Something up?"

Dean let out a deep breath and propped himself up on his elbows; "fuck life, man, seriously!"

"What happened? Did you scare him off with your big gay man-crush?"

"Scare who off?"

"Cas! What did you say?"

Dean frowned; "firstly, to you it's Castiel. And secondly, nothing... Much... Nothing I really regret. It's just... Unrequited love dude, it fucking sucks!"

Sam grinned; "Cas?"

"Yes! Obviously! Everyone says it's obvious, I thought Cas would have caught on by now but... Kid's too dense..."

"Well, we've all been hinting, we thought you were both too dense! So... Have you thought about actually asking him out?"

Dean scoffed; "no! For several reasons! "One: You know I don't ask people out, I don't take rejection well!
"Two: he's not in to me, he's like, anti-relationships.
"And finally: ...He's way too good for me. He could have anyone he wanted, if he wanted."

"Well, you're not wrong there, he is too good for you, but... I think, Dean, you should ask him out... Trust me."

"...Why?"

"Just, trust me."

Dean eyed him suspiciously; "what do you know?"

"Um..."

"Fine, keep your secrets!"

Sam sighed and pulled his phone from his pocket, sending a quick text to Gabriel; "Dean's just confessed. Step 2?"

Dean kicked his shoes off, dropped his jacket on to the floor, crawling under the covers; "don't stay up too long Sammy, it's late."

Frowning, Sam checked the time on his laptop; "it's half nine!"

"Whatever, I'm tired, and don't want your constant clicking keeping me awake!"

"Whatever!"

Dean mumbled something unintelligible in to his pillow before rolling over to face the wall. Sam sighed again and continued playing his game, waiting for Gabriel to reply. It took Gabriel nearly fifteen minutes.

"Just spoke to Cas, he's a little upset. What did your dick brother say?"

Sam frowned; "just that unrequited love sucks. What did Castiel say?"

"That he doesn't stand a chance, I'm not following right now? Dean definitely likes Cas?"

"Most definitely! He's sulking in bed right now. How shall we make this work?"

"Will Dean ever ask him out?"

"Not a chance in Hell."

"Damn. We'll have to do some serious meddling!"

"...What's this then?"

"Harmless meddling. Meet me tomorrow at 0830 by your locker! I'll strategize with Balthazar tonight."

"Haha, very good. Sam out!"

Sam glanced over at Dean, the rise and fall of his chest had slowed, so Sam assumed he'd managed to get to sleep.


Sam was putting some books in his locker when a pair of arms wrapped around his waist, stroking his stomach. Sam chuckled and turned to greet who he assumed was Jess, only to be met with Gabriel's grinning face.

"Gabe? What-"

"-Morning gorgeous!"

"What are you doing?"

Gabriel shrugged; "enjoying the view?"

"Get off me!"

Gabriel sighed and let go of Sam, taking a step back; "fine so... Balthazar and I managed to pull some kind of plan together, but we have no idea if it'll work or not..."

"All right, hit me."

"Right... Basically, you tell Dean Cas likes him, we'll tell Cas Dean likes him, get them together and make them kiss."

"You want to pressure them? Castiel doesn't look like he responds well to pressure."

"...He doesn't really, but it's the only plan we've got..."

"I know! What lessons do you have with Castiel but not Dean?"

"Physics, and Algebra, why?"

"Take Cas' phone, and text Dean."

Gabriel paused before grinning; "that could work! You're better at this than Balthy and I... But if it blows up in my face I'm blaming you!"

"Blame me. Anyway, I've got to get to home-room, so, let me know how it goes?"


Chuck noticed how down Dean seemed, when he slumped down in his seat, dropping his head on to his arms. Frowning, Chuck put his pen down and nudged Dean gently, waiting for the larger boy to lift his head.

"Are you all right, Winchester?"

Dean groaned and shrugged; "long night, didn't get much sleep."

"Oh, any reason?"

"My brain just wouldn't, stop! I spent all night running through hypothetical situations, each one as weird as the last..."

"What about?"

Dean looked down at his folded arms awkwardly; "nothing, important, just, you know... There's a certain time at night when your brain won't switch off, and wants to ponder the questions of the universe."

Chuck nodded; "yeah... But usually I have something specific on my mind. At the moment it's what direction to take my story in. Do I have my character swallow his pride and do what's best, or does he chicken out and miss out on something good? Or, does my other protagonist come out of his shell and take a chance, or just, continue being reserved and suspicious."

"...What are you writing?"

"A story. Don't be offended if I don't show it to you, no one knows what I write, not even Becky! It's a secret!"

Dean shrugged and rest his head back on his arms; "all right. Don't be offended if I fall asleep, I got none last night."

Chuck sighed and went back to writing. As attendance was being taken, Castiel glanced behind over at Dean, frowning at how the larger boy was slumped over his desk, looking worn out and frankly miserable, wishing he didn't have to bolt when the bell rang to get to the other side of school for his first lesson. Ever since he'd met Dean, he'd always seemed so chipper and upbeat, and it almost physically pained him to hear Dean non-committally grunt out something that sounded like "here" when his name was called. He went to pull his phone out to text his friend when the bell went; sighing loudly he grabbed his things and darted out of the room. Dean, meanwhile, finally lift his head from his arms, frowning when he saw Cas' seat empty. He managed to pull himself up and drag his uncooperative body down the corridor to his Art class. As he was flicking through a surrealism text book, his phone vibrated in his pocket.

"Are you ok? You looked terrible in home-room, it kind of worried me."

Dean couldn't help the small smile that found it's place on his face; "I'm fine Cas, just absolutely knackered. No sleep, full day of school, and I have work after."

"Why couldn't you sleep?"

"Lots on my mind, kept me awake."

"What kind of things?"


Castiel glanced over at Gabriel, frowning. He was doing less work than usual, and his usual inane grin was joined by a shifty look, he could feel him occasionally watching him.

"Gabriel," the smaller boy jumped at the mention of his name; "what are you up to!"

Gabriel began fumbling with something before shrugging innocently; "nothing."

Cas eyed him suspiciously; "you're acting strange... I mention how I was worried about Dean and now... What are you plotting!"

Gabriel held his hands up in defence; "nothing! What could I possibly be doing! I'm here, with you! Whilst Dean is, I don't even know where!"

"He's in Art."

"...Cas, are you actually going to tell him how you feel?"

Castiel's eyes widened; "no!"

"But the things you said he was saying last night..."

"They were just the normal things you say to a friend. He also kept saying when I get a girlfriend..."

Gabriel shrugged; "maybe he forgets you swing both ways? Well, every which way possible. And Cas, no one gives that speech their friends, unless they're hinting at something!"

"You think Dean was hinting at me to, ask him out?"

"Most definitely!"

Castiel leant closer; "you've lost your mind!" he hissed, before turning back to his work. Gabriel sighed and pulled Cas' phone out of his pocket, reading Dean's reply.

"I just feel crap after last night, telling you all that shit, getting all girly with my feelings, I feel like an idiot."

Gabriel paused to think what Castiel would reply with; "I'm glad you felt you could trust me, but I feel I need to correct you on something."

"I do trust you, I just don't trust myself. And what did I get wrong?"

"You said no one would "take you on"... You couldn't be more wrong."

"What are you saying?"

"I'm saying... Sam and Gabriel talk."


Sam was sat in Geography, idly tapping his pen on the back of his hand whilst the class was shown a video on the formation of oxbow lakes when his phone vibrated in his pocket, multiple times. He pulled it out under the table and saw he had several texts from Dean.

"WHAT THE FUCK DID YOU SAY TO GABRIEL!"

"I'M GOING TO FUCKING KILL YOU!"

"YOU'D BETTER NOT HAVE DONE WHAT I THINK YOU HAVE! YOUR BALLS ARE MINE YOU FUCKER!"

Sam's eyes widened, he was half amused and half terrified for his life. He nervously replied.

"I have no idea what you're talking about."

His response was almost instant; "BULLSHIT! CAS JUST TOLD ME YOU AND GABRIEL TALK! TELL ME WHAT YOU SAID!"

Sam sighed, he knew Gabriel was the one texting Dean as Cas, and wasn't amused he'd just dropped him in it. He sent texts to both of them.

"Why the fuck did you tell Dean we "talk" ? He's going to kill me!"

"So what if we talk? If you can be Cas' friend why can't I be Gabe's? And we just chat about everything, I told him you were a bit off last night."


Dean's hands were shaking in a mixture of fear and anger - Sam was supposed to be his brother, and certainly wasn't supposed to go and tell his crush's cousin he liked him! He had yet to text Castiel back, but he had no idea what to say; he had no idea if Cas was just playing him, or being condescending, or whatever. He finally got a reply from Sam.

"Maybe if you just asked Castiel out Gabe and I wouldn't have to interfere!"

Dean stabbed his pencil so hard on to the table the nib snapped off, he was also in danger of snapping it in half. He threw it on to the table and text his brother back angrily.

"Stay the fuck out of my love life! It's none of your fucking business! You'd better watch out or I'm actually going to kill you!"

Several moments later his phone vibrated again; "you're welcome, also: *Non-existent love life"

Dean managed to avoid everyone for the rest of the morning, refusing to text anyone back, trying to keep his mind on his work. He slumped down at the table already occupied by Chuck and Becky, dropping his head on to the top. Chuck frowned.

"Something the matter?"

Dean looked up, almost glaring; "fuck, my fucking life!"

"What happened?"

"My own brother has been conspiring behind my back! My life is over!"

Becky shared a look of concern with Chuck before reaching over and putting her hand on top of Dean's; "do you want to talk about it?"

"No! I want to curl up in a ball and die! ...But I have work later."

On the other side of the cafeteria, Sam saw Dean slumped at his table, and decided to go sit with Jess to avoid being killed. Before he sat he jogged over to Gabriel, who was stood chatting to Crowley in the dinner queue.

"Sammy!"

Sam frowned; "I think we've upset Dean."

The three boys looked over at the eldest Winchester, repeatedly hitting his head on the table. Gabriel bit his lip.

"Right... Might have to go explain a few things then..."

"Well, you might want to do it fast, Sunshine. Cas is going over," Crowley said, grimacing. Gabriel looked up.

"Shit!"

He jogged over to intercept Cas before he reached Dean. He got there just in time.

"Cas! Hey, forgot to give you your phone back!"

Dean looked up, watching Gabriel pull Cas' phone from his jacket pocket. Castiel frowned.

"You had my phone?"

"Took it first lesson, been playing on it, you know."

"Why?"

Gabriel shrugged; "giggles. Anyway, got to go before Crowley gives my place away."

He winked at Dean before jogging back over t the queue. Castiel and Dean shared confused looks, before Castiel sat himself down.

"Dean, I wanted to ask, are you all right?"

Dean began eyeing Cas suspiciously; "huh?"

"I was going to ask this morning, but didn't get chance to."

Surprisingly quick for Dean, he managed to piece together what had happened; "oh um, yeah, I'm fine. Just tired."

"You're sure? You look pretty... Annoyed, right now?"

"Nothing I can't handle."

"Ok, well... I was going to get food. Are you...?"

Dean shook his head; "you go ahead, I'm not hungry."

"Very well."

Leaving his bag behind, Castiel got up to join the queue. Ignoring the odd looks he was getting from Chuck and Becky, he pulled Cas' phone out and went through to the texts, to see everything Gabriel had obviously sent. He quickly deleted them to save Castiel the embarrassment; it also meant Sam was in less trouble. He was still in a lot of trouble, but he might just live to see another day. However, he was suspicious about how much Gabriel knew - obviously Castiel talked to him. If they spoke, and he and Sam spoke, and then Sam and Gabriel spoke, bad things were obviously going to happen. He'd need someone else to speak in confidence to, clearly Sam was a double agent.

"Dean, what are you doing?" Becky finally asked. Dean put the phone back where he found it and pretended to ack innocent.

"Just sorting something out... Gabriel was texting me from Cas' phone. I don't think Cas would like to know what."

"Oh... Did you tell him you like him?"

"No! Why would I do that!"

"So you do?"

"...Do what?"

"Like him!"

Chuck tried to stop himself laughing; "she's got you there, Dean."

Dean glared; "no. I don't like him! Like, that!"

Becky hummed dubiously; "whatever, Winchester."

Dean sighed and turned to see where Cas was in the line, only to be blocked by Crowley. He almost jumped off the bench, not expecting to see him in such close proximity.

"Dean, darling, I'm here to call in a favour."

"Oh God... What?"

A smirk spread across Crowley's face; "your phone. Give it to me."

"What? No!"

"Give me your phone, Winchester. You owe me a favour!"

"You're not having my phone! ...You and Gabriel are up to something!"

"Of course we are, now give me your fucking phone or I'll take it from you!"

Dean glared; "bring it on, love!"

Before Dean could even react, someone man-handled Dean from behind, whipping his phone from his jacket pocket. Dean spun around, Alastair was holding his phone up with a huge grin on his face.

"Sorry Winchester. When you owe Crowley a favour, you follow through!"

Crowley and his younger brother walked off to their table, leaving Dean to string together every curse word he knew in one breath. He turned back to face Chuck and Becky, who looked almost terrified. Still grumbling, Dean put his head back on the table, wishing the day would just end already. Castiel finally returned with his food, unaware of what had happened whilst he was gone. He did however notice something was up; Dean was being quiet, and Chuck and Becky weren't looking past each other. He nervously pushed his food around his plate, and watched Dean battle some kind of inner demon.

"...Are you ok, Dean? Like, really ok?"

Dean's head snapped round to look at Cas; "what?"

"Are you all right?"

"Um... Actually, no."

Castiel frowned; "what's wrong?"

"It doesn't matter..."

"Oh. All right."

Dean frowned too, feeling like he was betraying Cas by not trusting him enough to tell him what was wrong. Sighing, he played with his bag before getting up.

"I'll see you guys later, maybe not..."

He waved half-heartedly at Castiel, Chuck and Becky before walking over to the "Novak table". Crowley and Gabriel grinned when they saw him.

"I want my phone back tonight. Do your worst, I don't care any more. If he asks, I've gone home. Have fun."

Crowley looked up at Dean confoundedly; "where are you going?"

"Home. I don't feel good."

Before anyone could say anything else, Dean strolled out of the cafeteria, and down the corridor to the nurses office. He successfully feigned being ill and was sent home. He strolled the long way home, trying to distract himself with thoughts of homework, and cars he'd be working on later. When got in, he made himself a decently-sized sandwich, making himself at home in the front room, turning the stereo on as loud as he wanted as he settled in to doing homework. Luckily, his Chemistry work was complicated enough to distract him from any thoughts of what Crowley and Gabriel were saying to Castiel under his name. After all his work was done, he did a bit of tidying, so Bobby wouldn't be too angry he'd skipped school, before putting on his work clothes and heading to work early. Rufus was surprised to see him so early, but didn't complain.

"I'm not paying you overtime."

Dean laughed and pulled his overalls on; "don't worry about it, I won't do any work for you to have to pay me. I'll just work on my baby."

Rufus waved his hand; "take her round back, don't be cluttering my yard!"

"This beauty couldn't clutter anything, Rufus!"

"Whatever. Remember work starts at four, sharp!"

Dean nodded and hopped back in to his car, driving her round the back of the garage. Luckily for him, he and Rufus had the same taste in music, so it was no problem for him to blast AC/DC from his car's speakers as he tinkered with the engine, cleaning components and checking nothing needed replacing. He felt relaxed working on cars, they were simple, they didn't confuse him; his mood began to lift as he cleaned out the inside of his car - food wrappers, empty bottles and other bits of rubbish.


Castiel was sat alone in Biology, trying to concentrate on his work, but instead found himself missing Dean, who would normally be distracting him with his immature jokes about the text book's content. It didn't take long for him to pull his phone out and text him.

"Where did you go? Biology's not the same without you."

"Sorry, felt like crap, I'm at home, trying to get better before work."

"That's reasonable. What's wrong? I don't want to push, but being tired doesn't look like that."

"All right, I'm just feeling a bit off, after last night, I said too much."

Castiel frowned; "too much? What do you mean?"

"All that stuff I said about some girl being lucky to have you. I bet I sounded like a total idiot."

"Oh. Not at all, it was, flattering? ...Did you mean it?"

"Of course! I'm already a little jealous of whoever ends up with you!"


Crowley showed Gabriel the text he'd just sent Castiel from Dean's phone, Gabriel tried his best to bite back the laugh that threatened to erupt from him. Crowley grinned and waited for a reply.

"Sammy really has the best ideas! This is working, AND it's fun!"

"I've got to hand it to the moose, I didn't think this plan would work at all, but here Dean is, spilling his heart out to Cas..."

Gabriel laughed loudly, before slapping his hand to his mouth as the teacher shot a quick glare over at the two boys. The phone vibrated on Crowley's thigh. A large grin spread across their faces.

"Dean? I don't want to jump to conclusions, but... What are you saying exactly?"

Crowley went to type up a response, but Gabriel snatched the phone from him, deleting the message written. He wrote his own reply.

"Nothing, it doesn't matter, I've said too much, sorry, I shouldn't be bothering you with this, especially when you're in lesson. I'll see you tomorrow, maybe."

"Why'd you put that?" Crowley asked, taking the phone back. Gabriel grinned.

"Because, you don't confess your love via text. And because it's a good opportunity to get them together to confess their love in person!"

"Does Dean know Cas likes him?"

"I dropped enough hints. Besides, it's Cas that has to do the chasing, Dean's too chicken-shit to do it himself."

"What a girl."

The phone vibrated again; "I was already worrying about you, you're just making it worse Dean. You know you can trust me?"

"Don't text back, let Cas mull it over!" Gabriel said, grinning.


Four finally rolled around, Dean left the Impala behind the garage to get to work on clients' cars, whilst Rufus managed the phones and walk-ins. Unfortunately, the first car he had to work on was brought in by some arrogant business man, who clearly had no idea what was wrong with it, but refused to ask for help and began making things up, and certainly refused to be told what was what by some seventeen-year-old.

"There's this clunking noise when I turn the wheel."

Dean sighed; "yeah, your swivel bearing's blown."

"No, look kid, I had it check out not long ago, I had all the interior done up and everything!"

Dean took a moment to rub his face with his hand and collect his thoughts, knowing punching idiot clients wasn't good for business; "ok... Right, how about I get my boss to give her a look over? You can collect it tomorrow morning?"

The businessman nodded; "yes, very well. See that I get a written document from your boss about what's wrong."

Dean glared; "sure thing."

The man smiled proudly and left. Dean marched in to the garage to grab his clipboard and to have a small rant to Rufus.

"I hate those assholes! Just because I'm young, I know more about fucking cars than him! Oh, I had the interior done up not long ago! Well fucking done you moron! Ugh! He wants a written report from you on it, by the way."

Rufus smirked; "what's wrong with it?"

"Probably just the idiot putting petrol in when it should be diesel, he seems the type! But no, problem with the swivel bearings."

"Fair enough."

"Don't mention me, I said you'd do the work."

"Get to it then, want a drink?"

"Coffee, black, I'm going to need it if we've got more pretentious pricks booked in today!"

Dean went back out to the black Audi left by Pretentious Businessman and began to fill out the paperwork, before taking it in to the garage to begin work. He'd just found the replacement parts when Rufus walked in with his coffee.

"That kid's here to see you, again. Brought a party with him too."

Dean frowned and took a sip of his drink; "what? Cas is here?"

"I'll give you fifteen minutes, then they've got to go!"

Nodding, Dean went out to the front; Castiel was stood awkwardly by the front desk, Gabriel, Crowley and Sam were behind him.

"What's going on?"

Castiel looked up and frowned; "they dragged me here."

Gabriel grinned; "intervention time. Here's your phone, and now, you two need to talk!"

Gabriel shoved Dean's phone in to his hand and ushered Sam and Crowley out of the office. Dean motioned towards the chairs in the corner, he and Castiel sat awkwardly, avoiding each others' gaze.

"So, any idea what this intervention's about?" Dean asked, finally, taking another sip of his coffee. Castiel shrugged.

"I have a notion... Do you know why?"

Dean frowned; "yeah, I think I could guess."

"...Did you know Gabriel had your phone?"

"Yeah... Crowley took it from me at dinner. Did they tell you they were texting me from yours this morning?"

"Yes. They showed me the conversation."

"Great, now I'm the one that's behind... What did they say from me?"

Dean was almost too scared to hear the reply, so quickly brought up his texts, looking through the conversation. Castiel kept quiet, letting Dean see for himself.

"Sons of bitches," he mumbled, shoving the phone back in to his pocket. Castiel nodded.

"I'm so sorry."

Dean shrugged; "it's not your fault."

"Well, it kind of is... I told Balthazar, who told Gabriel and Crowley. They instantly began plotting, and then, included Sam the other day apparently."

"Told Balthazar what?"

Castiel sighed; "you're really going to ask me to say all of this? Out loud?"

Dean sighed too and rubbed his face; "all right then, I'll guess, stop me if I'm wrong?"

Cas nodded, biting his finger in anticipation. Dean cleared his throat, took a large gulp of his coffee before beginning.

"Ok... You told Balthazar that... You liked me?"

Castiel nodded.

"So, he told Gabe and Crowley, and since then, they've been plotting ways to get us together? That dinner for example?"

Cas nodded again.

"And so, their big shit-eating grins were because they knew?"

Another nod.

"They decide to recruit Sam to speed things along on my end, and I sort of go and put my foot in it by telling him I liked you..."

Another nod, accompanied with a flush on pink to Cas' cheeks.

"And then, today they tried to get us to indirectly admit it to each other whilst they pretended to be us, only for us to be sat here now?"

"...I think you've got it all."

Dean nodded and finished his drink; "great... So now what?"

Castiel shrugged; "I've never been in this position. Ever."

"If I'm honest neither have I... What do you want to happen?"

Castiel looked at his feet, Dean got up to put his empty cup on the desk, watching Cas play with his tie awkwardly. He glanced over to the window and saw Gabriel, Crowley, and Sam watching them. Sam was scowling at him. Suddenly, his phone vibrated in his pocket. Sighing, he quickly looked at what Sam felt needed to be said.

"Ask him out you idiot! He's too shy to do it himself!"

Letting out a deep breath, Dean rubbed his face and dropped his phone back in to his pocket. He stuck his fingers up at the boys grinning at the window, signalling for them to go away. Frowning, they all trudged away from the window, giving the two boys some privacy.

"Cas?"

The smaller boy looked up, his hands visably shaking. Dean managed a small smile and took one of his hands, pulling him up, not letting go.

"You've only known me a week, Cas."

"And you've only known me a week."

"...Touché."

Castiel stared in to Dean's eyes, finding it hard to concentrate when he felt Dean's thumb stroking the back of his hand softly.

"You know, I understand that you're new to all of this and... Well... I'm fine with taking it slowly if... You... Want?"

"...Meaning?"

Dean smirked; "you're really going to make me say this?"

Castiel bit his lip to stop himself smiling, he nodded.

"Ok, fine... Castiel Novak. Would you do me the honor of being my, um, boyfriend?"

Cas paused, staring in to Dean's eyes before nodding; "of course."

"...Awesome... Can I, hug you?"

A big smile spread across the smaller boy's face; "if you wish."

Dean hesitated, taking a moment to note the happiness in Castiel's face, before letting go of his hand and slowly wrapping his arms around his waist, pulling him closer so their bodies were pressed together. A large smile of his own spread across his face when he felt Castiel's arms snake around his neck. Letting out a deep breath he wasn't aware he'd been holding, Dean hid his face in the crook of Cas' neck, closing his eyes and enjoying the moment; only for it to be ruined a few seconds later by Gabriel, Crowley, and Sam barging in to the office, cheering a clapping.

"About damn time!" Gabriel grinned, wrapping his arms around Dean and Cas like a proud father. Castiel's face instantly glowed bright red, whilst Dean scowled at the intruders. He was going to shout at them when Rufus walked in to the office.

"Right boys, time to go, Dean's got some work to do."

Crowley and Gabriel groaned but knew not to push. The five boys walked out of the office, Dean and Castiel walking behind.

"I'll talk to you later," Dean said, in a hushed voice so the others wouldn't hear. Castiel managed a small smile.

"You can't leave me with them."

"I'm sorry, but, I do have to work."

"I know... Well, I'd best let you work then."

Dean quickly took Castiel's hand in his, rubbing it with his thumb before pressing his lips to his knuckles; "you'll be fine."

Cas smiled fully, his hand tingling where Dean had kissed it; "until tonight."

"Until tonight."

They stood staring at each other, fingers loosely intertwined, until Gabriel shouted at Cas to hurry up. They shared another smile before going in their separate directions.