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Sam has a problem. That problem takes form in his best friend and his brother and the fact that they have been dancing around each other for YEARS but both of them seem to think that their feelings are unrequited which Sam and anyone else with a working set of eyes can see is obviously not true. At first, when Sam saw they were interested in each other he had hoped they would never get together assuming that their relationship would be awkward and that he would constantly be a third wheel because even though Cas was an angel he was practically living with them because he disobeyed Heaven, so Sam would have virtually no way to get away from them and their lovey-dovey bullshit. After a while, though, Sam stepped back and evaluated himself and realized that in the grand scheme of things, he only cared that Dean and Cas were happy. He was on cloud nine for a while after this realization, to realize that Dean and Cas were not in fact any closer to being in a relationship than when they first started flirting.
Sam spent months after that looking for signs that Dean and Cas's barely platonic relationship had blossomed into a romantic one. He found none. That was about two years ago. It was also when Sam first started developing a plan to get them together. He stopped soon after assuming that with everything going on, maybe Cas and Dean were aware of their mutual attraction but just weren't ready for a serious romantic relationship. Sam was quickly proven wrong though, when they made their home in the Men of Letters Bunker and the world was no longer ending and Cas was a full angel again.
Sam supposes that this is some kind of divine punishment for wanting Cas and Dean to stay friends when they obviously had feelings for each other Sam now realizes that the only thing worse than third-wheeling for a couple is third-wheeling for a couple that doesn't realize they're a couple. Recently, Sam found a book in the bunker's library titled Angels and Their Unique Needs. This book inspired a second wave of plotting that Sam plans to act on this time.
It takes Sam about two weeks to finish the book, normally it would have taken longer but he spent every waking hour reading, ultimately deciding that a couple of lost hours of sleep would be better than watching Cas and Dean awkwardly dance around each other any longer.
Sam got a bit worried that Dean's attraction to Cas was one-sided after beginning his reading. Angels by nature tend to be tactile creatures constantly seeking out any contact they can get. This is likely a result of an increased natural skin hunger but an inability to fulfill it because of the limitations that come with human vessels. Apparently, in their true forms outside of a vessel touch is much easier. My sources suggest a vessel is like a physical barrier between an angel and the world around them unless the angel chooses to press themselves closer to the skin (according to my sources there is no better way to describe it in any human language.) in which skin to skin contact is much easier to feel, but angels tend not to press close enough to the skin in a vessel to feel the full extent of touch unless they feel completely safe because it leaves them vulnerable as a result angels who remain in vessels for extended periods tend to be starved for touch. Cas is relatively affectionate compared to Sam and Dean, but not nearly enough if the book should be taken as fact Sam files that information away for later as he reads on . Angels court much differently than humans do mostly because angels were (most likely) not designed to feel any kind of attraction. Therefore I can only speculate that the very idea of courting is a learned behavior in angels. I theorize that most angels still don't feel any form of attraction whatsoever but in the angels that do it seems to manifest commonly as the following factors: staring (I presume the staring results from angels being able to see souls and that whatever attraction they feel may be linked to that), acts of service, and attempts at imitating the behaviors of the one they wish to court. Sam is practically vibrating out of his skin as he finishes reading. His worries about Dean's heart being broken are vanquished because Cas checks all the boxes for angelic courting.
Sam thinks back to all the times Dean had scolded Cas for staring at him ”Cas, man are you trying to smite me with your eyes.” ”No Dean I would never not you, never to you.” Cas’s voice had softened at the end of the sentence his words pitched in a way they only ever were with Dean. Dean had mistaken Cas’s tone for one of shame. ”It’s an expression I know you wouldn’t hurt me, Angel.” Dean had winked at Cas at the end of his sentence and Sam knew he was flirting. He had seen Dean flirt with enough girls to pick up on the signs, Cas on the other hand just tilted his head in confusion before eventually the moment had been erased as Sam had redirected the conversation.
Sam thinks of the way Cas has always attempted to please Dean, the way he would come anytime Dean called, the way he would do things without telling either of them all to make things easier for Dean, the way anytime he messes up he attempts to reconcile by doing the laundry or buying groceries.
Sam thinks of how Cas picks up on the things Dean does and tries to copy them, like how he drinks beer with Dean even though he can’t really enjoy the taste or get drunk. Cas also listens to the same music as Dean even though he has admitted frequently that he doesn't understand it.
A couple more sleepless nights are had on Sam’s end before he finally comes up with the perfect plan to get Dean and Cas together. Finally, about a month after Sam had originally found the book, he knew what to do about Dean and Cas.
Sam got up in the morning and walked into the kitchen where he found Dean turned toward the stove cooking something that was most definitely bacon and of course, Cas who was sitting at the table staring at Dean before quickly averting his eyes as Dean turned to face Sam. “Good Morning.” Sam yawns as he greets them.
“Yeesh, Sammy the bags under your eyes gotta go on the bottom of the plane.” Dean laughs before turning back towards the sizzling frying pan and flipping the bacon.
“Dean is correct, Sam you do seem to be lacking sleep.” Cas says from his seat at the table before continuing his task of staring at Dean.
“You guys really don’t need to worry. I've just had a little trouble sleeping the last couple of nights. You know how it is.” Sam informs them as he walks to the fridge to retrieve a salad he had made the day prior. After retrieving his salad and a fork, Sam sits at the table but not in his usual spot. This time he sits right next to Cas. Their shoulders are practically touching. Cas glances at Sam for a second but doesn’t say or do anything because he doesn’t really mind. Dean soon finishes cooking and brings a plate of bacon and scrambled eggs to the table sitting in his usual place which is directly across from Cas he looks at Sam his eyes slide over to Cas and narrow just slightly Cas doesn’t notice, but Sam does. His plan is working out perfectly because Sam knows that look in his brother’s eyes underneath the layer of confusion, there is jealousy.
The moment doesn’t last long because Sam finishes eating soon after Dean sits down but he makes sure that as he stands his shoulder purposefully brushes against Cas’s “Hey Cas?” Sam asks as he walks towards the sink to wash his dishes “Can you meet me in the library later? I need some help with a topic I’ve been researching.” Cas nods an affirmative and as Sam leaves he catches the look on his brother's face this time the confusion is gone and in addition to the jealousy he can see the competitiveness, the determination, and something that looks like hurt.
Of course Sam feels bad about tricking his brother into thinking he has a crush on Cas, but he just knows it will get them together. Him and Dean fought over girls and they’ve had massive prank wars that went on for weeks and every time Sam backs out first and Dean is persistent. Sam knows that the competitiveness in Dean that drives their sibling rivalry will make an appearance soon and Sam’s suffering will be over.
As promised Cas meets Sam in the library Sam doesn’t actually have any super pressing research that makes it necessary for him to enlist Cas’s help but he did have some research that he may or may not have just pulled out of his ass at the last minute to give some credence to his request for help. Cas, of course is not as naive as he was years ago, points out that Sam does not in fact need any help. Sam mentally takes a deep breath and tells Cas his perfectly crafted excuse of wanting to spend time with him, he lays it on thick telling Cas he’s jealous of the fact that he and Dean are so much closer and how neither of them talk to him or spend time with him nearly as much as they do each other.
Cas’s face softens “I’m sorry Sam I didn’t realize you felt so left out.” Something complicated flickers over Cas’s face before carefully hidden by the concern and guilt that was present on his face before. “From the beginning I knew Dean and I shared a more…” he trailed off.
“Profound bond?” Sam asked, recalling Cas’s words from all those years ago.
“Yes.” Cas says, giving Sam a little half smile. In that moment Sam understands just for a second what Dean sees in Cas. Sam sees how far Cas has come from the apathetic Angel to the Cas he and Dean know and love.
When Sam stops to think about it he realizes that what he said to Cas wasn’t just an excuse to get him to stay in the library with him. All at once Sam realizes that if Cas and Dean do get together Sam may lose his best friend and brother at the same time that, in order to be happy, Dean and Cas will leave him behind.
“Sam”
Cas’s voice cuts through his thoughts and it’s only after he comes back to himself does Sam realize Cas is in front of his chair crouching down so their eyes can meet. Cas’s hand hovers close to Sam’s face, unsure what to do. “Are you hurt, do you need me to heal you?” Cas questions Sam as his eyes move from his hand to Sam.
“No it’s fine Cas” Sam says his voice breaking from the tears that are now falling down his face “I’m not hurt there’s nothing for you to heal, I’m just” he sniffles a little “I feel like you and Dean are so close and eventually you’ll leave me alone because you’re happier without me.” Sam hadn’t meant for it to go like this; he just wanted Cas to spend time with him alone to make Dean jealous enough to make a move on Cas.
Cas’s eyes manage to soften even more “Sam, I don’t know where you got the idea that me or Dean would ever leave you.” Cas almost seems to tear up before continuing “My brothers and sisters abandoned me easily after I chose Earth over Heaven. I never knew my father but when I met him he saw me as nothing more than a pawn in a game only he can make moves in. I wasn’t designed to have free will and I had to fight to get it I made bad decisions and got You and Dean hurt many times but you guys never abandoned me you showed me that family is more than what you can do for people and how well you follow orders, you proved to me more times than I can remember that no matter how many times I try to walk away or do things on my own that you will always be there for me. Sam, until I met you and Dean I never had that, I never had unconditional love. I didn't know that siblings could love each other even after they did something wrong. You and Dean gave me everything when I had nothing I would never abandon you for anything and I know Dean wouldn’t he’s died and gone to hell for you Sam, most parents wouldn’t even do that for their own children if they knew the torture and trauma it would entail but Dean did it for you with no hesitation.” Cas’s eyes are misty by the time he stops talking.
Without warning Sam lurches forward closing the short distance between him and Cas, hugging him tightly “Thank you.” he says glad for the reassurance.
Despite being shorter Cas finds a way to readjust their positions so that Sam is the one being held, tucked against Cas. With the way they are positioned Cas’s back is toward the door but Sam can see out into the hallway. Sam, of course, only pays attention to this when he catches a glimpse of Dean in the hallway peering in. Dean averts his eyes quickly and walks away. Sam knows that Dean probably didn’t see him looking at him but he briefly entertains the idea of pushing Cas away and attempting to explain what is going on to Dean, but he doesn’t.
Eventually Sam and Cas let go of each other and part ways. Sam thinks back to the moment and realizes that Cas had quite literally melted into the hug when Sam first grabbed him before eventually switching their positions. Sam quickly flips through the book before rereading the paragraph from before about angels being tactile creatures and needing to be vulnerable Sam instead focuses on the phrase “skin hunger” which he had not paid much attention to the first time he read it. Sam has heard the phrase before but he can’t really remember what it means.
Sam spends a couple hours researching skin hunger and realizes that Cas’s reaction is concerning. The way Cas reacted implies that he doesn’t get nearly enough skin to skin contact in other words Cas is touch starved. Sam desperately wants to be surprised but he knows deep down that it makes sense. He and Dean were raised by a physically and emotionally distant father and no mother they didn’t get hugs as congratulations for good work, they didn’t climb into bed with their father when they had nightmares, all they had was each other and Dean wasn’t that much older than Sam he barely remembered what a normal childhood was like, there was no way he could give one to Sam.
Sam and Dean hug and slap each other on the back and of course they gradually dragged Cas into their dynamic, but that was nowhere near enough especially since Cas refuses to let himself feel safe so he never feels the full extent of the contact anyway.
Sam once again changes objectives this time instead of attempting to Dean and Cas together for his sanity he’s doing it for them, he’s doing so that Dean can finally feel like good things can happen to him, he’s doing it for Cas’s health so that he’ll finally feel safe enough to let himself get what he needs, he’s doing it because he wants them to be happy.
That night Sam is sitting in the library with a random book he thought would be interesting when he hears familiar footsteps. Sam looks up to see Dean in the doorway.
“We need to talk.” Dean’s eyes are serious as he looks at Sam.
“About?” Sam questions as he marks his page in the book and closes it.
“You.” Dean says before sitting across from Sam.
“What about me Dean?” Sam asks exasperatedly he’s already emotionally drained and feeling guilty, which usually are feelings that accompany any “talks” he has with Dean.
Dean must catch something in Sam’s tone because he seems to almost get defensive, a sign that if Sam doesn’t play his cards right this “talk” will turn into an argument.
“I saw you and Cas in the library earlier.” Dean blurts out.
Sam is stunned for a minute; he hadn't expected Dean to ever confront him about Cas; he just kinda expected him to initiate some kind of silent competition, a war for Cas’s attention.
Sam realizes that Dean had never stopped talking: “You have to be careful, Sam, I don’t want you to get hurt you know he’s an angel you’re probably expendable to him-”
“Dean what the fuck are you talking about do you hear yourself right now?” Sam interrupts.
“I can’t believe you think so little of Cas after everything he’s done for you, for me , for us and you think he would just abandon us?” Sam is desperate to understand Dean. Deep down Sam knows that Dean must be projecting his feelings onto him, but he wants to hear what Dean has to say for himself.
“This is different.” Dean's response is almost robotic like he’s repeated to himself a million times.
“What is different?” Sam is still angry but now his voice waivers, he’s unsure, he’s never heard Dean sound like that before, never heard him sound so defeated.
“A romantic relationship. Jeez Sam you can’t honestly think that an angel is gonna want to stick around a human you hear how they talk about us, Sam, we are nothing to them.” Dean is fiddling with his hands as he stares Sam in the eyes.
Sam had long abandoned the notion that this conversation was going to be civil, but now as Dean stares into his eyes Sam can see that this is a cry for help, a way for Dean to blow off steam.
Sam doesn’t get the chance to respond because Cas walks into the library telling them that when he went into town earlier he heard that there was a potential hunt for them. Dean gets up and leaves with Cas almost immediately leaving Sam to ponder his thoughts while he puts the book he was reading away before joining them.
The hunt is a simple salt and burn and the only reason they end up being away from the bunker for three days is because of the drive to another state and back. Things are slightly awkward between Sam and Dean throughout the whole time they’re away from the bunker, thankfully though, Cas doesn’t notice anything amiss.
Two days after the hunt ended Sam hears a knock on his door while he’s rereading the book he found about angels and thinking about how he can get Cas to let his guard down enough to accept the affection he so obviously needs.
“Sam.” It’s Dean, he sounds hesitant, almost timid.
Sam takes a breath and walks over to the door, after stashing the book in his drawer, and opens it to reveal a guilty looking Dean.
“Can I come in?” Dean asks.
“Yeah.” Sam walks further into the room allowing Dean to enter.
Dean follows Sam into the room and closes the door behind him.
“Look Sam I’m sorry for what I said a couple days ago I just don’t want you to get hurt. I trust Cas with my life and I know you do too. I just still can’t believe that he would want to stick around, you know, he’s so inhuman and sometimes I guess that kind of scares me. I mean you’ve heard how the other angels talk about us and about humans in general. I guess I just thought that somewhere in Cas he thinks like that too, I mean they must have been raised like that, right?” Dean seems almost defeated as he voices what sounds like thoughts that have existed in his mind for years, his eyes focus on the ground instead of Sam but Sam can tell his apology is genuine .
“Dean, I forgive you but you can’t seriously think that Cas would abandon us for anything. I mean he left heaven for us. The other angels are his family Dean and he chose us over them. Also you can’t possibly believe just because he was raised to think that humans were an inferior life form that he still thinks so. I mean neither of us would ever try to kill Cas right and we were raised to hunt and kill anything that wasn’t human, right?” Sam is desperate to get Dean to understand what Cas said to him in the library, he needs Dean to understand but words never mean much, too many false promises and bold lies have forever tainted words for both of them but somehow Dean is more reluctant to let himself trust.
Sam can’t stand to see his older brother look so defeated ever since they were small Dean always seemed unshakeable, in the face of monsters, in the face of their father, and now Sam realizes, in the face of his own feelings.
“Sam I know you like him but you have to consider the possibilities—”
“God Dean I don’t like him and I’m sorry I made you think that. I know you like him. I just wanted you to make a move. I didn't expect it to get this out of hand. I just wanted you to realize your feelings toward him.” Sam interrupts Dean.
Dean’s mouth opens a little like he’s going to say something but Sam stops him again.
“You really can’t deny it Dean, I know you too well.”
Dean’s mouth closes and opens again, this time Sam lets him speak.
“And you’re fine with that?” Dean questions he sounds almost suspicious.
“Why wouldn’t I be?” Sam is confused as he questions his brother.
“It’s….” Dean stops for a moment, obviously unsure what to say. “Strange.” Dean finishes but he doesn’t sound sure.
“Why? Because he’s my friend, an angel, or a guy.” Sam asks.
“Kinda all three I guess I mean he is like your best friend. And a human and an angel? Dating? That sounds like the beginning of a bad joke. Him being a guy and all is sorta odd too I guess.” Dean pushes all his words out in one breath, his eyes finally meeting Sam’s.
“I’m not going to lie to you Dean at first I was annoyed at the potential of you two dating because I thought it would be annoying going on hunts and constantly moving around stuck as a third wheel, but I thought about it and decided that I wanted you to be happy even if that happiness means I’m a perpetual third wheel.”
“Regardless of whether I like him or not there’s no way he likes me back.” Dean’s eyes are back looking at the ground as he wrings his hands together anxiously.
“He totally does man, haven’t you seen all the staring he does.” Sam is shocked that Dean doesn’t think his feelings are reciprocated; he supposes that looking in on their relationship from the outside is different from being a part of it.
“Those are just little quirks “angel things”” Dean says making air quotes.
“Yeah angel courting things.” Sam informs him as he gets up to get the book from the drawer he stashed it in.
“What courting, bullshit, even if it was how would you know.” Dean is now looking at Sam again.
Sam turns to face him and drops the book open to the page about angels courting onto Dean’s lap.
“I only tried to get you to make a move because I knew Cas liked you too.” Sam crosses his arms as Dean’s eyes periodically widen as he reads.
“He likes me too.” Dean’s voice is like a whisper, disbelieving and awestruck.
Sam smiles as Dean rereads again and again.
“Why hasn’t he done anything?” Dean’s mood seems to sour in an instant.
“Because you’re both dumbasses who don't think the other could possibly like you back.” Sam rolls his eyes as he talks.
“I should go talk to him.” Dean starts to get up.
Sam smiles before speaking. "I believe in you Dean.”
“Yeah, okay now we’re getting cheesy.” Dean smiles back before getting up all the way up and walking to the door he puts his hand on the knob and starts to turn it before he turns around to look at Sam “Thanks by the way.” He says. Then he opens the door and leaves, closing it behind him.
Sam sits on his bed and contemplates what had just happened. He hadn’t expected to show Dean the book, he also hadn’t expected Dean to dump all of his emotional trauma surrounding Cas on him but hey, now Dean will most likely make a move on Cas and their long awaited relationship will finally begin.
Sam notices that Dean and Cas’s relationship stays mostly the same for about a week. He starts to doubt that Dean ever actually talked to Cas at all.
That all changes when one day Sam goes to ask Dean if he needs anything from the store. Sam knocks on Dean’s door three times with no response which is odd because it’s the middle of the day, as hunters they have a relatively hectic sleep schedule but sleeping in the afternoon is practically unheard of at least for Dean, so Sam assumes Dean’s just trying to be a dick so he opens the door to a crack. He is equal parts shocked and excited at what he sees, Dean and Cas cuddled up on Dean's bed, asleep.
Sam shuts the door quietly and practically runs out to the car before celebrating, as quietly as possible, his success.
As he’s driving, Sam gets a little worried about Cas sleeping. He thinks about it and theorizes that because of the whole touch starved thing that Cas was simply overwhelmed and went to sleep.
When Sam gets to the store, he picks up the regular groceries and a couple extra pieces of pie to congratulate Dean on his newfound, and hopefully lifelong, relationship.