Sam comes up with a perfect plan. In time he sees firsthand how it can all go so wrong, but in the moment it's an absolutely brilliant plan and the finishing touch (after a flourish of pen) just walked through the door.

"What're you doin', Sammy?" Dean asks, walking towards the table where Sam's set up, hunched over with far too many colored pens. San covers the paper, all but laying over it, and does his best to look both embarrassed and annoyed. It's incredibly easy with all the practice Dean's given him over the years.

"None of your business."

Dean clicks his tongue before following the path Sam's set out for him to a 't'. Mouth curving into a knowing grin, Dean plays his part "A love note then."

Sam rolls his eyes, looking over his work before carefully folding it along the marked seam.

"Need any tips there, Sammy?" Dean nudges him, wiggles his eyebrow in that way that just scream dork to Sam but somehow gets girls to swoon.

"No, no tips." Sam looks contemplatively at the card, lets the moment drag out, adds a dash of worry, a note of anxiety "but…"

He almost feels bad at the flip that tone causes in his brother, how the teasing and ribbing morphs quickly into Dean's 'make it better' mode, parental nurturing instead of sibling foolery. But Sam only uses it for Dean's own good, so who can blame him?

"What's up, Sam?" Dean leans against the table, gives Sam his full attention. Sam tries his hardest to mask the 'I know something you don't' smirk that tries to break through and instead look earnest.

"I'm just not sure if I can go through with it, you know?" Sam sighs and looks away, this is harder to do than he thought, what with Dean looking all concerned, "It-it's a guy." He glances up quick, like he's worried, "and he's older than me—not by much just a few years—but…

"I don't know, I just don't know if I can give it to him, you know? What if he says no right there?"

"Sammy," Dean puts a hand on Sam's shoulder, it's warm and so familiar that Sam suddenly feels much younger, "I know I give you a hard time, but you gotta know that anyone'd be lucky to have you, boy, girl—anyone. You're a good kid and if they don't want you, then that just means there's someone a hell of a lot better out there for you."

It's fake, the whole situation is fake, but Sam can't help that his chest feels warm at Dean's words, that he's reminded again that even if their dad's never around, he's so lucky the world gave him Dean.

"T-thanks, Dean." Sam clears his throat, tries to get back into character, "but I still don't know…um, could you…?"

"What?"

"Could you give it to him?" Sam gets out in a rush, "please? He's in your grade so it shouldn't be a problem and just knowing he has it, that'll be enough, even if nothing comes of it. Please?"

Sam's trying to decide if puppy dog eyes would be too much when Dean rolls his eyes, "sure pipsqueak. First one's on the house. But any more and you gotta give 'em yourself. Can't have your big brother passing your love notes."

"Thank you thank you thank you!" Sam says, shoving the card into an envelope and sealing it, "tomorrow?" He asks, handing the sealed letter to Dean.

"Yeah, Yeah," Dean says in fond exasperation looking down at the letter now in his hands, "Who's it going to anyway?"

Sam doesn't miss a beat. "Castiel."

"Cas?" Dean probably doesn't know how quick his head shoots up at that, because if Sam hadn't been sure before (he totally was) he would certainly know now that his big brother has the largest crush on Castiel 'Cas' Novak.

"Yeah," Sam smiles, "he's just so…" he makes a hand gesture, vague and meaningless. Sam's sure Dean will fill it in appropriately.

"Yeah…" Dean says, subdued. He looks back down at the letter with an almost forlorn expression on his face and Sam wonders if this will be it, if Dean will refuse to give it to Cas and they'll have a talk about Dean's feelings. But he doesn't, just keeps glancing at the envelope as he walks towards his room, stubborn as always, but that's why the letter is even there, the foolproof plan is in motion. Sam would worry about that, about the fact that Dean is willing to give a love letter to the boy he loves from his brother at the detriment to his own happiness, about Dean's willness to kill his own chances at happiness for the vaguest chance that others around him will prosper in his stead, but Sam is thirteen and all he knows is that he has the best damn plan to get his oblivious pining brother together with Cas—who is equally, nauseatingly, smitten.

Castiel likes school. He enjoys learning, stupid as it sounds. He likes talking about the stuff he's learning with his friends and get different perspectives. He's generally a good student and averagely popular, nothing particularly singular to make him stick out for better or worse. That's why this is such a surprise.

"Well, you gonna take it?" Dean hold out the blank envelope, shaking it a little in emphasis.

It's not that Castiel has never gotten a love letter (which, to be clear, he hasn't), but that he's being handed one by Dean. Dean is… well, he's amazing. Since he moved to the area, it's just been one enamoring thing after another. He's fabulous in English, great at machines, is nice to everyone, is really helpful even when it's detrimental to him, is handsome and fit, and he can sing really well (Castiel is pretty sure he's not supposed to know that, but tough he does, and it's only made his crush on Dean impossibly worse).

Dean's lip quirks up and oh that's what's off, since Dean stopped him in the hall to hand him the note, he's looks disgruntled, like he's doing something he doesn't want to. Now that he's smiling a bit the contrast is so striking that Castiel can't help but wonder what's wrong.

"Just take it you weirdo." Dean rolls his eyes, pushing the letter into Castiel's hand, looking down at it as he does. When he catches site of it, the smile falls off his face so abruptly that Castiel looks down too, because surely there's something wrong. But all he sees is an envelope. A slightly crumpled, blank and sealed envelope.

"Dean, what's wrong?" Castiel asks, looking up, because he's not sure if he even wants it if it puts that expression on Dean's face. But Dean's already gone, leaving Castiel alone with the letter and the overwhelming desire to tear into it and never touch it all in one.

He waits until he's home at least. Castiel tried to get some of his homework done first, in case it wasn't the kind of letter he thought it was and it would just ruin his concentration. But after fifteen minutes spending more time looking at the white envelope instead of page 120 of Slaughterhouse 5, Castiel gives into the reality that it has already ruined his concentration and goes over to his desk.

Careful not to rip the letter inside, Castiel opens the envelope. The letter is odd. Not anything like what he'd think Dean would do. But—and his chest fills with fluttering warmth at the thought—love does crazy things to people.

Each word is a different color. And—he notices—go in a rainbow pattern. They're subdued, nothing too vibrant or eye exhausting, but obviously a time intensive endeavor.

Castiel

I've liked you for a long time now, but didn't know how to tell you until my brother suggested a letter. I'm not that great with words, but writing is easier than trying to say it out, so here it is: I like you, a lot. Please go out with me.

All my love.

It's nothing like how Dean talks, missing his personal accent and the rhythm of his words. Castiel would have preferred it, he thinks, if Dean would have just told him, it would have sounded more real somehow. But he can't blame him. After all, Castiel has been crushing on Dean since almost the time he moved into the area and he certainly hasn't said anything about it. So maybe a letter was easier, that's fine. It certainly gives Castiel some time to think over his words—even though the most important one in this instance (YES) would have been very easy to come by.

A letter for a letter then. Castiel's not the best at the written word, but then neither is Dean it would seem. He'll give it to him at the end of school tomorrow, and maybe include his number so they can text, pick a date for a date. Castiel finds himself smiling rather stupidly and he can't help feeling embarrassed, even here alone in his room. Nothing for it. Castiel nods to himself, grabbing a good piece of paper and gets to work, leaving his school work untouched in favor of a more important assignment.

He'll have to tell Dean tomorrow that he really much prefers it when Dean calls him by the nickname 'Cas'. Castiel seems so weird coming from Dean, even in written form.

Dean hasn't really been in a good mood lately, to say the least. Day before yesterday he learned that his little brother had a crush—great right? Older siblings wait for the day they get to tease their younger siblings about their infatuations. Not in Dean's case. Of course it wouldn't be that easy in Dean's case. No, Sammy, his actually kind of awesome little brother had to go and have a crush on Cas, a really awesome, kinda nerdy, super fascinating guy that Dean just so happened to be nursing a crush on since they moved into this Podunk town. Of fucking course.

When did Sam even meet Cas, for christ's sake? They're three years apart, it's not like Sam spends a lot of time loitering around the west side of the school when all of his classes are in the east building. But of course it would be Dean's luck that his brother would somehow pick Castiel out of a crowd to have a crush on. And of course Dean would fucking volunteer to deliver Sam's damn love letter to Dean's crush.

So yeah, the last two days haven't been that great. Dean's been working on compartmentalizing, on shoving his feelings into a little box so he'll be able to act happy when Sam comes to tell him all excited that he and Cas have a date and thank Dean excessively for delivering that first fucking letter in the story of their love affair. He hasn't been able to do it yet, hasn't gone much past being slightly nauseated, really, but he thinks he'll have it down by the time they announce their wedding and that's something at least.

Oh god, Dean's going to have to give Cas the big brother speech, full of threats and creative violence if he ever dares to hurt Dean's brother and Dean doesn't know if he'll be able to do it because he kind of also wants to give Sam that speech, because Cas may have an army of older brothers, but they're never really around and he doesn't have someone looking out for him like he should. Oh, here comes the nausea again.

Dean slams his locker shut with a lot more force than necessary, but the loud clang forcibly clears his mind, so that's something.

"Dean?"

It's Cas, of course it's Cas. And of fucking course he looks great, big blue eyes, rumpled button up because he plays with the collar when he's nervous, lip chapped and pale, and a look of worry on his face. Worry for Dean because Dean's acting like an idiot throwing a temper tantrum.

Dean schools his face into something of a smile but if Cas asks for his blessing or some shit he does not want to be held responsible for his stomach's choices.

"Hey Cas."

That settles Cas a little and he gives a smile back, fingers fiddling and catching Dean's periphery. In Cas' hands is a blank envelope, sealed and crisp but for the corner he's worrying absentmindedly. Dean's stuck on it, the crispness. It's definitely not the one he gave Cas yesterday.

"This is for—"

"Sam." Dean cut in. Has to cut in or he'll go insane.

"What?" Cas sounds startled, probably because Dean's being so damn rude because of course Cas would give him a letter to give to Sam. Hasn't Dean already established that it's very rare that the west and east buildings come together? It only makes sense that Dean would be the go between—living with Sam and all. At least Dean won't have to watch them walk the halls hand in hand for at least another year.

"Sam," Dean babbles, unable to shut his fucking mouth because this is weird right? It's really weird and Dean can't take his eyes off that crisp white envelope and how Cas' fingers are still now, not fidgeting in the least, "it's your answer to Sammy's love letter from yesterday, and it's a heck of a lot easier to give it to me then track him down yourself, especially because I gave you the letter from him because he was being a bit of a wimp—not that that's bad or anything, just that he should have probably given it to you himself but I get it because it's hard sometimes to share your feelings in case they're not returned and you can be a little intimidating, so it doesn't reflect bad on him that he was a little timid alright? And it worked out fine anyway right?" Dean gestures to the envelope to make his point, hating and unable to stop the high little laugh he lets out at the end that's all tension.

Cas' hands have tightened on the envelope and it's not so pristine now, Cas' fingers making shadows play across the surface. But if Dean were Sam, he'd want that letter, even if it was a little rumpled because it's from Cas so he holds his hand out dutifully, a sense of de ja vu falling, except he hadn't felt this strung out yesterday when it had still been only a possibility and not a reality.

Cas pulls the envelope closer in to himself, bringing it up to his chest and further from Dean's hand. Dean looks away from the letter finally and to Cas' face. It's clear how red he'd been before due to the absence of color now. White as a ghost.

"N-no." Cas takes a rocking step back, eyes looking everywhere but at Dean. Great, he scared him off with that weird ass little speech and now they won't even be able to be friends. It pangs, right in the chest, even as he thinks that maybe it's for the best. Dean's not sure he could be just friends without always wanting more. Better to not torture himself, there's enough of that going on.

"No, it's not ready." Cas say firmly, turning on his heel and leaving Dean standing like an idiot, hand outstretched for affection that wasn't even for him.

Castiel feels like an idiot. He feels stupid and hurt and-and… god how could he have been so stupid? Of course Dean wouldn't… and hadn't Castiel though that the letter wasn't like what Dean would ever do at least thrice and he still went with the fantasy that Dean—

So stupid.

When Castiel walks into his room he finally unclenches his hand, the scrunched up letter mocking even in its current state. To think he didn't get any work done yesterday because he wasted all his time on the stupid thing. Castiel tosses it in the trash, intent on forgetting this whole thing ever happened and catching up on the work he put off for nothing.

He gets further than yesterday (which isn't saying much), but it's like the thing is insulting him from the trash. Castiel does the only thing he can, and calls up Meg.

They meet in the woods behind their respective houses that serves as a barrier between their two neighborhoods. Castiel brings the original letter he'd been given (how did he ever think Dean would write in rainbow?) and the one he wrote, seal unbroken.

Meg brings the lighter.

It's a thing they do, when awful experiences take physical form like this, the best way they've found to deal with it is cleanse—with fire. Castiel is going to burn the letter and it'll make him feel better about being pathetic when there's no evidence—at least for a little while. He isn't sure if he's going to burn the first one. It seems incredibly rude to Dean's brother, but given the circumstances and the lack of a signature at the end, well its certainly up for debate.

For now though, for now it's serving as a prop as Castiel tells Meg the whole bit. When he's done, feeling embarrassed and indignant and devastated all in one due to the retelling, Meg lets out a long whistle.

"First," She starts, looking him straight in the eye, "I'm a little insulted that when Mr. I'm-so-hot-Clarence-has-had-a-crush-on-me-forever gave you a love letter your first action wasn't to call me."

"Well I would have felt even more foolish getting excited over it with you when it turns out it's from Dean's little brother."

"Mhh that would have been disappointing."

"It's disappointing enough as it is, thanks."

"How old is the little Winchester anyway?"

Castiel lets out an exasperated breath, this has been bugging him too, "I don't even know! Meg, I don't even know Dean's brother's name! How can he have a crush on me when I don't think I've ever seen him before in my life—at least not with knowing who he was."

"Poor Clarence, attracting admirers without even remembering the faces of those he bewitches."

"Me-eg" Castiel drags it out with a whine.

"Come on now, sugar plum, you know I'm just mean because you're special, now come here." She holds out her arms. Castiel takes a moment to register it for what it is, an invitation for a hug, because Meg is so sparse with blatant affection outside of her barbed words wrapped in velvet.

"Haven't got all day."

Castiel takes the cue and goes in for a short, hard hug, "I'm sorry it wasn't really from Dean, I know that sucks, and I am here for you in whatever violent capacity you'd like."

"Thanks Meg."

"Us rebels have to stick together," she winks, "now come on, lets burn some shit."

"Dean!" Charlie spots her freckled compatriot down the hall, "we still on for this weekend? I've got the extended edition and enough pop rocks to take half the town."

"Hey Charlie," Dean give a small smile, much too small for someone who's been made aware of just how many pop rocks are at their disposal, "I don't know, things have been kind of…" he makes a gesture that means absolutely nothing.

Something's very wrong, Dean doesn't resort to hand gestures unaccompanied by vocals unless it's something real important, something he really doesn't want to talk about but really, really needs to if he wants anything to get better. The thing about Dean and talking about emotions and the like though, is that though he really, really should, he really doesn't like to. Getting him to open up is all about tact.

Of which Charlie possesses none.

"What's wrong?"

Dean shrugs, "I dunno, just haven't really been…" Another meaningless hand gesture.

"Okay, let's get out of the hall and have this non-discussion somewhere else."

Dean follows her easily enough, and Charlie thinks that whatever it is, even Dean might realize he needs to talk about it.

Alone in the E wing which is all but abandoned on Tuesday and Thursdays, Dean tells Charlie all of it and Charlie listens, and the further it goes, the more confusing it gets.

"Why in the world would you—" she starts.

"I know! I must be masochistic right? That's gotta be it, no one in their right mind woulda done that." Dean buries his face in his hands, a groan leaving him.

"Yeah you really gotta look into that, Buddy." Charlie pats him on the shoulder, "But I don't get why Sam would do this at all? He's been head over heels for Jessica for forever."

Dean looks up at her, "No? He told me all that Monday, why the hell would be fake it? To what, embarrass me? He's the one who wrote the stupid letter."

"I don't know, Dean, it just doesn't make sense."

Dean lets out a huff with no humor in it, "wishful thinking. Like I could get that lucky."

Charlie can't do much about it now, but, looking at Dean hunched over and feeling miserable, she vows she will. If anyone can get to the bottom of this, it's Charlie. For now though…

"Hey, screw English, let's head to the game store, I bet we can get Garth to let us start messing around early."

"Oh god, I can't go to English, Cas is there."

"O-kay. And we are leaving!" Charlie jumps up, "Come on handmaiden, haven't got all day."

Sam hasn't really been avoiding Dean apart from the fact he kind of has. The timeframe for this master plan shouldn't be all that long, but, in the meantime, Sam can't be in the same room with Dean without smiling conspiratorially. Sam's not sure what Dean could do, even if he found out what Sam had done, but he doesn't really want to find out. So in the library on Friday, Sam does not expect to run into Dean. It's the perfect place (it also helps that Jess is here, studying for French—like she even needs to, really she's so good).

That's what makes it all the more surprising when Charlie comes over in a flurry of movement—and purpose.

"Hey," Sam smiles, "Dean's not—"

"I want to know why you're writing love notes to Cas when I know for a fact that you have a crush the size of Jupiter on Jessica."

"Charlie!" Sam sputters, an octave too high. If Jessica hadn't heard what Charlie said, she definitely heard that, and she's going to think he's an idiot.

"Well?" Charlie sits across from him, "it better be a damn good reason because Dean's miserable and you could have really screwed things up for him."

"What—no—it'll be fine, Charlie," Sam said, forcing himself to whisper as he divulges his plan that's starting to seem a lot less perfect the more he says and the stormier Charlie's face gets. Dean being miserable certainly wasn't in the plan. Cas was supposed to get the note, think it was from Dean, and then tell him he liked him, then they'd go out and Dean would owe it all to Sam, and Sam would be able to lord it over Dean for forever. Apparently, according to Charlie, that's not at all how it's going.

"Fix it." She says as she stands, menacing in a way Sam didn't think Charlie could ever be until this moment. He nods rapidly and she's stalking away, like the gust of wind she came in on.

Sam's sitting there dumbfounded, starting after her, until a quite clearing of the throat catches his attention.

"So, I hear you have a crush on me 'the size of Jupiter'?"

Sam doesn't think his face has ever been so red.

"So," Sam says with about as much casualty as a sledgehammer in a glass house as they're eating dinner (alone again, Dad out on business), "heard from Castiel?"

Dean has to take too tries to force his bite down his throat, as dry as it suddenly is, "No. Came up to me yesterday with a note but said it wasn't ready." Dean takes a breath, has to keep going now before he can't "and look, if you have any more notes or anything, give them to him yourself okay? I mean what kind of person passes out his brother's love notes?" he gives a forced little laugh.

Sam looks at him, so sad, that Dean all but swallows his tongue ready to say forget it and offer his services again, even if is driving him a special kind of crazy.

"I don't like Castiel, Dean."

"What?" Dean says, flat, because he doesn't know what he's supposed to be feeling right now.

Sam looks embarrassed, "I wrote that for you…from you. I-I didn't sign it, and you were giving it to him so I knew he'd think you wrote it, 'cause I know you like him but you wouldn't ever say anything an I heard he really likes you too. I just wanted to make you happy."

"…oh."

Sam waits, obviously expecting more, expecting anger because he did manipulate his brother and it ended awfully.

"I…" Dean says, lost in thought, "I said it was from you. When he went to give me the letter, I told him you wrote it. Does that mean he…?"

Sam feels terrible, "It was for you."

"Oh." Dean stares down at his place, "so now he thinks…" Dean tries to work through it—not even what happened as much as what he's feeling. It's like he's a yo-yo getting tossed around and now he's all tangled. Sam doesn't like Cas. That's good. But Cas thinks Sam likes him and by extension that Dean doesn't like him, which couldn't be more wrong. That's bad. That Cas doesn't know. He's gotta tell Cas. But after all this, does Cas even want to… and does he even like…? That letter, that crisp white envelope with the worried edge because Cas was nervous about giving it to him, even though Dean had (supposedly) confessed already, that was for him. God.

"I'm gonna…" Dean leaves, heading to his room.

After all this, the only thing he can think to do, to explain, is to write a letter.

Monday comes and Castiel is glad he had the weekend to deal with all of that. It's not better, by any stretch, but manageable. Luckily he doesn't have English with Dean today and he does have Chem with Meg, so things should be okay. Time heals all wounds and all that, right?

"Cas!"

Castiel stops in the hall and turns, even though he knows who it is, even though he knows he shouldn't. Oh God, he hasn't even though about an answer to Dean's brother, has he? How to tactfully word 'I'm sorry, I really like Dean, not you'?

"Dean" Castiel nods a little, bringing his books closer to his chest with one arm and fiddling with his collar with the other as Dean comes to him.

Dean looks like he's trying to find out if he's allowed to smile, lips twitching in and out of the motion until Castiel offers his a small smile and Dean sinks fully into the action. Is it really fair that Dean has to be so handsome? Especially when he's playing messenger for the Winchester that Castiel doesn't want.

"Hey, so, um," Dean starts, a little laugh leaving him as he tries to find his words and that's when Cas sees it. A while envelope, blank. He can't do this again, he really can't.

"Dean, I don't like your brother."

"Good."

"I don't even know his name—wait, good?"

Dean's grin is shy, pink's rising to his cheeks, "yeah, really good." he clears his throat, "This is—umm" he shakes the envelope a little, "this is from me. For you. Because I like you."

Castiel fells almost physically dizzy with confusion, "What?"

Dean flushes scarlet, "I explain it all in this," the letter again gestured with, "but safe to say my brother's a nosy little shit and he knew I liked you so—" Dean cuts himself off. Shrugs.

"So, this is from you."

Dean nods.

"For me."

Another.

"Because you like me."

Dean looks away as he nods. God, his blush is pretty.

"I just have to make sure, because the last time I thought that I was wrong."

"Yeah, I'm really, really sorry about that. Sammy is too."

"Well," a little giddy laugh burst forth, "at least you don't write in rainbow." A beat. "You don't, right?"

"He wrote in rainbow? God, I'm gonna kill 'im."

"At least go on a date with me before you commit murder, I don't want to visit a jail."

Dean's smile gains a little more surety (did he really think Castiel would say anything other than yes?) and he looks stunning, "yeah? That mean you like me too, Cas?"

Castiel feels the heat to go his cheeks and he knows he must look ridiculous, smiling so wide, but too happy to feel embarrassed about it.

"Maybe," Cas plucks the envelope out his Dean's hand, "maybe you should ask me out to be sure."

"Cas," Dean steps a little closer, "would you go out with me?"

Cas has a grand idea of dragging it out, flirting more blatantly and pretending to think on it, to need persuasion, but that's not what happens.

What happens is this: "Yes."

Thanks for reading! If you liked it please let me know :)

I haven't been writing much lately (working on some longer stuff but it's hard to keep the motivation, as I'm sure y'all know), but I opened word this evening to write out the plot of this after getting home from an entirely too long day and instead of bullet points i was writing dialogue. when that happens, best to just go with it. But, though it is now much later then when I wanted to go to bed, it was fun to write and I hope you enjoyed reading.

Best.