AN: Prequel of sorts to my fic In Which Sam Winchester is Absolutely Clueless

I think it's particularly hilarious that this is longer than the original story I posted... But I was just thinking about how all these guys could be so friggin *oblivious* to what's so friggin *obvious* and I decided to explore a little bit :)

Mary watches as her son and Castiel rush through the kitchen, grabbing sandwiches on their way out to the backyard. Cas has agreed to help Dean practice football. Cas might not be on the team - his own interests in astronomy club and chess team don't give him time - but he's always ready to help Dean improve.

John is helping her finish up the dishes. He's lost in his own thoughts, which allows Mary to allow her own to wander. She watches the boys through the window, laughing as they throw the ball and tackle each other. Her imagination takes those images and replaces them with another, then another, until she's watching her son walk down the aisle.

A wistful smile is on her face before she realizes just what she's thinking.

Oh.

Oh!

"John?" He hums in acknowledgement. "Do you think maybe Dean has a thing for Cas?"

Her husband starts and nearly drops the bowl he's washing. "Uh, what makes you say that?"

"Mother's intuition?"

"Oh." A pause. "No."

She's a little annoyed that he'd shoot down her fantasy so quickly. "What makes you say that?" And if a little of her irritation slips into her tone, well, she can't quite help it.

John actually looks nervous. "I uh, I asked him about it."

"You asked him?" Seeing John clam up a bit, she pulls back on the scolding tone. "Well, what did he say?"

Defensively, he grumbles, "If you're going to give me shit for asking the boy, I don't see why you should get to benefit from my snooping."

Mary laughs slightly before gently putting a hand on her husband's soldier. "I'm sorry, I'm not trying to tease you or anything. I'm just surprised that you of all people would try to have a heart to heart with your son about this." Satisfied with the shy smile she receives, she then adds, "You can't say something like that and not expect me to be curious."

John relays the conversation. How he asked if Dean's dating anyone right now (he's not). If there were any pretty girls (or boys) in his class he's interested in (there isn't). If he and Cas were just friends or if-

"Wait, what? You actually said that?"

"Yeah?"

Oh my god, Mary is mortified on behalf of both her husband and son in this moment. She hopes that John interprets her red cheeks as surprise because she can't even begin to explain why that was such a silly idea. So instead she asks in a strained voice, "And what did he say to that?"

"Well, I think he looked downright shocked but sounded honest enough when he said they're just friends. And that he doesn't feel like that about him."

Mary just sighs and nods a bit. John takes that as a, "Yes John, you are absolutely right. Good detective work there. What would I do without you?" Really, it's cute that he's trying. But Mary's not convinced.

Oh, she doesn't think John or Dean is lying. She's just aware of how young Dean is. He's only 15! And while he might think of himself as all grown up, she knows better. That his experience with matters of the heart are limited to a couple passing crushes and a fierce loyalty to his family. In a few years, Dean might just realize how fond of Cas he is and exactly what that fondness means.

So she just goes back to drying the dishes, occasionally looking up to watch the boys playing. To hope that, no matter who Dean ends up with in life, that they'll share the sort of easy friendship he currently has with Castiel.

Over the next few years, though, her belief in the matter wavers. Nothing really changes. The boys obviously love each other, but there's no words or actions that lead her to believe that they're in love with each other. So though she fosters a hope for something she can't quite define, she lets it go.

(John will bring that discussion up with Dean years later, an accusing tone in his voice. Dean looks away sheepishly and explain that he didn't think about Cas that way... until John had put the idea in his head. Then it was pretty much all he could think about. And a few years later, he'd learn that Cas felt the same way.)

Becky and Chuck always had brunch together on Saturday afternoons. Something quiet for just the two of them. And there was never really a fear of interruption - Castiel never work up before noon, and even if he did, he's usually out the door to spend time with Dean.

Speaking of...

"So," Chuck says slowly as he carefully spreads some raspberry jam over a slice of toast with way more focus than the task requires. "Castiel and Dean..." and he kinda just leaves it at that, not sure how he wants to broach the topic.

Becky doesn't say anything, just gives him a questioning look.

With forced aloofness, he continues. "They're really close." She nods slightly but doesn't say anything. "Like... surprisingly close?" Nope, she's still just looking at him like he's an idiot (and he does feel like an idiot right now). "And I was just wondering if you thought that maybe they were uh... more than friends?"

Becky stops mid-bite and her eyes light up. Yes, this was more the reaction he'd been expecting. She's about to spit her food all over him, he can tell, and she's going to just start gushing so he holds up his hands and immediately adds, "I'm just asking, I don't know anything! It's just a thought! Please do not make a thing about this!"

She's practically bouncing in her chair as she hurriedly finishes chewing and then washes it down with some orange juice. "Oh no you don't, you know something if you're bringing this up-"

He wilts a little under the accusing tone and very aggressive finger pointing currently aimed at him. "It's just... I hear they're going to prom. Together, maybe? And it got me thinking and..."

"Together?" is all he gets before she erupts in squeals and claps enthusiastically. "Oh my god, my baby is-"

"Becky." He tries really hard to sound stern. Although she doesn't look any less excited, she at least stops and waits for him to continue. "I'm not actually sure if they're going together together. John seems to think they're just going together because they didn't get dates and it's cheaper to buy tickets as a couple or something."

Her expression drops slightly in disappointment. Becky takes a moment to think about it, before asking, "Well, what does Mary think?"

He shrugs. The conversation was just him and John, so he doesn't really know what Mary's view on it is. But... well, now that he thinks about it, Mary was there when they'd been talking about it. Mary has no problems with correcting her husband of silly assumptions, so he doubts she would've stayed quiet unless she agreed.

"I think," he says slowly, "that she's either not sure or doesn't think they're dating."

With a deep sigh, Becky collapses back in her chair and lets out a quiet, "Oh."

"So, like I said, I was just wondering... what you thought...?"

This was a bad idea. He's made his wife upset bringing this up, and for what? To gossip about their son's possible romantic entanglement with the boy next door?

Finally, Becky straightens back up and continues her brunch, a determined look on her face. "I'll look into it."

Which she does. For weeks. She doesn't want to be too direct in her questioning, afraid of embarrassing her son or exposing an awkward situation between the boys. Because she's always thought there was that potential. But what if there's some sort of unrequited interest on one side or the other? Or maybe they're both just genuinely not into each other like that and her asking makes them uncomfortable and damages their friendship?

Chuck is actually impressed with the delicate care she takes in her questioning. Asking about Dean, making suggestions. Gentle prodding. It gets them nowhere.

"So... do you boys plan on wearing boutonnieres?"

He tries not to perk up with interest as he subtly tries to watch their son's reaction.

"I don't know?" But no, Castiel is distracted by his homework and his expression gives nothing away.

"Maybe you should get Dean something green for his. To bring out his eyes."

At this comment, Cas looks up in concern. "Is that important?"

"I just thought it'd make him look a little extra handsome."

Cas' brow knots in confusion. "I don't really think that's necessary." He goes back to doing his homework, "But I'll mention the suggestion."

With their son's face effectively buried in a textbook, Becky throws her husband a look of pure exasperation and a dramatic eye roll. These boys, she mouths at him.

Prom comes and goes, and nothing really seems to change. Becky and Chuck just shrug at each other and agree that the boys must just be good friends. Oh well.

(Of course later when they find out, Becky frowns in confusion. Brings up this very conversation and how Cas just seemed so disinterested. Cas frowns back, then explains that, "Dean's already the most handsome person I've ever met, the added flourish seemed an unnecessary addition." The look Becky shares with Chuck at that is priceless.)

Bobby sifts through some of the prom pictures Mary sent his way after Dean's prom. They're all pretty standard - the boy and his friends standing in front of the house, on the stairs, in front of the limo. Though there is one of him and that neighbor of his that makes him lift an eyebrow. They're standing kinda close together. The angle's wrong to really see, but he'd swear they're holding hands.

"Hmmm."

"What's that?" Ellen looks up from the inventory she's doing.

"Oh, nothing. I think Dean's dating that Cas boy."

Ellen just shrugs. "Yeah, probably. Those two are crazy about each other."

"Mmm," he agrees as he continues to thumb through the pictures. "Don't say nothing 'bout it to John, though. The man's an idjit and will just try to interfere. Say something stupid and scare the boys off."

She snorts. "No shit."

Jo kicks him under the table again and he nearly loses his cool and yells at her to just stop.

They're in the Winchester kitchen working on a project. Well, he and Jo are working. Ruby is playing on her phone and complaining about the teacher. Thus all the kicking. Jo didn't want to work with Ruby but Sam, hormonal teenage boy that he is, leaped at the chance to offer a spot in their group.

And yeah, she's not necessarily contributing a whole lot right now... But she is smart, she'll help out eventually.

("Sam, you can't just invite her to work with us because she's pretty."

"I swear, Jo, that's not why-"

"Shut it. You owe me one.")

Another half hour and Jo gets fed up. She's about to snap, about to say something that's going to ruin any chance he might have with Ruby but again it's not about dating her, he just thinks she's nice really he swears.

"How 'bout we get a snack," he says in a rush, nearly jumping out of his seat. "I think we've earned a timeout."

"Sure," Ruby says as she continues texting. "I could use a break."

"You have to actually work to need a break," Jo mumbles but luckily Ruby doesn't hear. Or doesn't care.

Sam pulls out a bag of chips and cookies, then gets everyone a drink. Once they've settled comfortably back at the table, they eat quietly. Jo, apparently done with sulking, perks up suddenly. "Oh! I forgot, isn't Dean moving out this weekend?"

"Yeah. He already helped Cas move in a couple days ago, but he's not done packing up his stuff. There'll probably be pizzas involved if you wanna help carry some boxes."

For the first time all afternoon, Ruby seems genuinely interested in their conversation. "Your brother's moving in with Castiel?"

"Yeah, they got a place downtown by the college."

"That is so hot."

Jo and Sam share a bewildered look. "What?" Jo asks, but Sam's pretty sure what she means is a very loud, "What the actual fuck are you talking about?"

"Dude, Sam's bro is fine. That Castiel is a little quiet for my tastes, but he ain't exactly hard on the eyes. And the two of them, living together, going at it whenever they want." She does a dramatic full body shiver. "Like I said, really fucking hot."

"Going at it?" Later on he'll be proud how even he kept his voice. Because seriously, what?

"I mean, if you were living with your boyfriend, wouldn't you be all over him all the time? Or girlfriend, I guess, in your case."

"Boyfriend?" Sam squeaks at the same time Jo gags out, "Oh gross!"

"They're uh, they're just friends Ruby."

"Bullshit. Didn't they go to prom together? And now they're moving in together? Totally fucking each other."

Sam is pretty sure he has never blushed this hard in his entire life. "Uh, they went to prom as friends. They're just friends. Good friends. They're not dating or... or..." There's no way he's going to say the f-word in reference to his brother and Cas for Christ's sake! "They're not," he finishes lamely.

Ruby raises her eyebrows skeptically at him before laughing a bit. "Sure, Sam."

And that's probably when he decided he wasn't going to try and date Ruby. He'd been so thrown off by the whole thing that he couldn't look at her without going bright red. And maybe it makes him close off to the idea of Dean and Cas dating, wipes it away as a possibility. Keeps him from noticing all of the things.

Most notably that Dean and Cas' new apartment only has one bed.

("Oh my god," Jo all but shouts at the end of that fateful Christmas dinner. "Ruby was right!"

"Ugh, do not make this worse for me."

After a quick explanation, Dean does indeed confirm that, "Yeah, we fucked like every day in like every room for a month. It was awesome."

"UGH!" Sam throws his hands over his ears in a desperate attempt to un-hear all of that. "Just stop.")