Headcannons hurt sometimes...

Sam and Gabriel dated for years. 

Dean never knew.

He never knew that Sam fell in love with the archangel, and that Gabriel loved him back twice as much. The two would sneak out together every chance they got. Whenever Dean would run off with some girl while they were hunting, Sam would just call Gabriel, and they would run off on an adventure of their own.

Gabriel, being the Trickster archangel he was, loved to do things for Sam. He'd zap the Winchester to Paris, London, everywhere in the world that Sam wanted to go. Sometimes, it was just to somewhere as simple as a bookstore, where Sam would browse and read books that weren't about lore, for once. Gabe didn't care much for reading, but he was happy to sit back and watch Sam freak out over the pieces of paper. As long as Sam was happy, he was too.

Gabriel even created them their own little world, monster free. Whenever Sam wanted a vacation, or just a break from the hunting life, Gabriel would take him there, to their own little house in a supernatural free world.

It was Sam's favorite place.

Sure, it was just a small blue house, nothing special, but Sam loved it. He loved being able to wake up in a bed next to Gabriel, knowing that nothing was going to attack them, and  no one was going to judge their relationship. 

They'd spend weeks in that house, plying games, having prank wars with each other, watching movies- anything they could think of. There was a lot of kissing involved too, but this is Gabriel we're talking about. You can imagine the things he'd do with Sam and no consequences.

And whenever Sam felt good enough to return to the hunting life, Gabriel would zap him back, barely a minute passing between the time he'd left and returned.

It was the long hours spent with Gabriel, in that house, that kept Sam from getting hopeless and depressed over the hunting life. Time with Gabriel made him happy, and it gave him life light.

Dean didn't have that. That fact made Sam sad sometimes, because he knew that Cas would be willing to give Dean everything, if Dean weren't so stubborn, but there was nothing he could do, Sam knew. 

Dean had to work out his feelings for Cas for himself, the same way Sam had worked out his feelings for Gabriel.

Sam and Gabriel were happy together, happy as could be. But then Lucifer got involved, and Gabriel had died.

Or so Sam had thought.

Watching the archangel die was the worst thing Sam had ever experienced- even worse than Jess. Sure, Sam had loved Jess too, but Gabriel....

Gabriel meant so much more.

Sam stayed quiet as he and Dean drove away from the hotel where Gabe had died.

"You okay?" Dean finally asked, as his brother stared blankly out the window.

"Gabriel's dead." Sam admitted, the words themselves stabbing at his heart.

"I know." Dean replied. Dean wouldn't understand- Sam knew that. If Dean knew what Gabriel had meant to him, he might have understood, but not now. "But Sammy, think about everything he did to us. The dude was a general dick."

Sam thought about it. Oh, how he thought about it. He remembered the times that Gabriel had tricked them. He hated Tuesdays and Asia forever because of it. But those weren't the only memories of Gabriel that Sam had.

He remembered the loveable smirk on the angel's face.

He remembered how it felt to be with him, and how Gabriel would look at him like he was better than a world's supply of candy.

He remembered what it was like to be in that house with Gabe, the rest of the universe away- just the two of them.

He remembered what it was like, waking up and seeing Gabriel's golden eyes staring at him in adoration. 

He remembered how Gabriel would suffer through long hours at bookstores he found boring- how he'd watch dull French films because Sam thought they were interesting.

Sam remembered how much Gabriel loved him, and how much he loved him back.

That was why his death hurt so much.

But Dean didn't know any of that.

Sam glanced back out the window, knowing there was nothing he could say. Anything else, and Sam would just start crying, and Dean would know something was up.

And Sam didn't really feel like bawling and trying to explain to his brother how much he loved the archangel that had killed Dean over a hundred times.

He knew Dean wouldn't approve, anyway.

He and Gabriel had both known. He had even asked the angel about it one day, as they laid lazily on their bed in their little house, oblivious to the rest of the world.

"What's on your mind, moosie?" Gabriel had asked, his head resting on Sam's chest as the Winchester studied him.

"Do you think I should tell Dean about us?" Sam had blurted out. The idea hadn't left his mind. Part of him thought Dean would understand- that he'd approve, and even admit that he liked Cas.

"I don't know if that's a good idea." Gabe had offered. "Dean....You know he doesn't like me very much."

"But maybe he'd change his mind if he knew." Gabriel snorted.

"Sam, if you told your brother you were in love with me, he'd hate me even more, and threaten me quite colorfully."

"No he wouldn't."

"Your brother is a protective mother bear, and you are his cub. He would rip me limb for limb if I even lightly offended you." Sam paused.

"Okay, that's true." He admitted. "But I think he might be happy for me. He always talks about something more, Gabe. About one of us leaving the hunting life- getting married and living that dumb apple pie life. I know that he wants that life, Gabe, not just for himself, but for me too."

"But I'm an angel, Sam. Marrying me would only drag you further into the mess of the hunting life. The other angels kill people who fall in love with them."

"Cas is an angel too." Sam commented. "I don't see Dean having a problem with that."

"But we also don't see Dean acting on his obvious feelings for Cas." 

"....Cas doesn't have an issue with us."

Yes, Castiel knew about Sabriel. Gabriel had to brag to someone, didn't he? And who better to shove that news at then the angel who was also desperately in love with a Winchester, but couldn't get anywhere with his relationship? 

Cas and Sam never talked about his relationship with Gabriel, but Sam knew he didn't mind. Gabe had admitted that Cas even threatened to kill Gabriel if he messed things up with the younger Winchester.

But it looked like Cas wouldn't have to kill the archangel- because he was already dead.

Or so they thought.

Until the day that Gabriel was dumped off at the bunker, and Sam's heart just about exploded.

Seeing Gabriel the way he was- tortured, his mouth sealed shut, broken- it made him want to cry.

And cry he did, privately, when he knew Dean wouldn't be looking for him.

He tried his best to patch up the archangel, the blow that Gabriel had been alive the whole time stinging even more when he found out what Gabriel had been doing.

He hadn't tried to contact Sam once. And that stung.

But then Gabriel had come back, and he killed Asmodeus. And Sam had hoped that the angel he loved was back for good.

But then Gabriel had left again, leaving Sam alone with his ruined heart.

Cas had tried to comfort the Winchester, but he had no idea what to say or do.

Sam didn't even know what there was to say that could've made him feel better.

Gabriel had shown up again, later, when the rest of the bunker was asleep.

Sam had stared at him, not knowing what to say. 

Gabriel had stared at the ground, knowing that he had messed up. That he had broken his love's heart.

"You're what kept me alive." He whispered. "Through everything." He glanced up at Sam. "I still love you, Sam." Sam shook his head. 

"I thought you died." He insisted. "And that broke my heart- You broke my heart, Gabriel."

"I know, and I'm sorry." Gabriel truly did look sorry. "I'm so sorry, Sam."

Sam shut his eyes, everything becoming too overwhelming. Everything, with Lucifer and Jack and this whole alternate world- and now Gabriel? It was a bit too much to handle at once. Sam needed to step back. He needed a break. He needed-

He needed that house.

And he needed Gabriel.

"I need a break, Gabe." Sam whispered. Gabriel nodded. His grace was weak, but neither of them really cared. 

They spent three weeks in their house, escaping the messed up world they lived in for one where the only problem was between the two of them.

Slowly, Sam mended his heart, and Gabriel did everything he could to try and win back his moose. 

Slowly, they fixed each other. And then they went back, knowing that they couldn't hide from the world forever.

And then Gabriel had died, for real this time.

Somehow, having his angel back for such a short time, only to have him ripped away again, hurt even more.

But Sam distracted himself. Distracted himself from Gabriel's death because it was the only thing keeping him from tumbling into a pit of despair. He focused on finding Dean, figuring out how to kill Michael, making sure everyone else was okay and had a job to do.

Sam Winchester focused so much on everything else, that he forgot to eat and sleep. Those things just seem unnecessary when you're dead inside.

But then Dean had come back, they hit a dead end with Michael, and things calmed down a little bit.

And finally, one day in the library, Sam stopped focusing on everything else, the weight of Gabriel's loss fully hitting him like a truck.

He froze, staring blankly at one of the bookcases, not knowing how to breath.

Dean glanced up from his computer, frowning at his little brother.

"You okay?" He asked, as realization slammed down on Sam.

Gabriel was gone. Possibly, and probably, forever. And there was nothing Sam could do.

The angel he loved was officially dead.

But Sam knew that he couldn't just say that Gabe was gone, and expect Dean to understand. He'd have to explain first, make Dean know how much Gabriel meant.

And for once, Sam thought that he should. He knew Dean would never fully approve of a relationship between him and Gabriel, but Gabriel was gone now. There was nothing Dean could do either.

"No." He whispered, his eyes going glassy as he shook his head and turned to face his brother. "I'm not okay."

Dean closed his computer, focused on his brother, waiting for him to elaborate.

"I...." Sam's voice cracked, tears filling his eyes. "I don't know what to do now."

"Sammy-" Dean started, but Sam shook his head.

"No, Dean, you don't understand."

"Then help me to." Dean looked worried now. The brothers so rarely showed emotion in front of each other- watching Sam cry was like a beacon that something was terribly, terribly wrong.

"Gabriel is dead." Sam offered, his voice shaking. "I don't you don't care about that- but I do." He clenched his jaw. "I care about that so much, Dean."

"We barely knew-"

"NO, Dean. YOU barely knew him. I knew everything about him." Sam declared. "I spent a lot more time with him than you did, and he meant a lot more to me then he did to anyone else." Dean stared at his brother, puzzled.

"Gabriel...." Sam struggled, trying to find the words to make him understand. "Gabriel was my Cas." 

Dean froze, fully understanding. Sam sunk down in a chair, unable to say anything more as he covered his face with his hands, hiding the tears falling from his eyes.

"It'll be okay." Dean told him.

"No it won't."

"You're right." Dean agreed. "But it will get easier, Sam, I promise." Sam wiped at his eyes, looking at his brother.

"It never gets easier." He retorted. "Do you honestly think that losing Charlie, or Bobby, or Kevin, or Jo- or EVERYONE we have ever lost has gotten easier?"

"No." Dean studied his brother. "But we find a way to move on from their deaths. Somehow, we move on enough to get out of bed in the morning and get on with our lives, no matter how much it hurts." Sam shook his head.

"Gabriel WAS my reason to wake up in the morning. He was my outlet, Dean. He was what made this life bearable, and now he's gone."

"But he wouldn't want you to sit and cry every day for the rest of your life, now would he?" Dean questioned. "Gabriel would want you to live your life." Sam snorted.

"Gabriel would probably laugh his head off if I spent my life mourning him."

"No- he'd slap you for it, and you know it. He'd tell you to not be a coward." 

".....I loved him, Dean." Sam whispered. "I still do, and I think I always will." Dean nodded.

"That will never change." Dean insisted. "Every time we lose Cas- hell, I've just stopped even trying to get over him when he dies. I've just accepted that I'll always care about him, even if we lose him forever."

"But Cas comes back, and Gabriel won't." 

"You don't know that for sure." Sam nodded. In the hunting life, they really didn't know. Sam wiped the tears from his face.

"Can I give you some advice?" He asked. Dean frowned.

"Sure."

"Losing Gabriel is probably the worst thing I've ever experienced." Sam began. "But when he was alive, and I was with him?" He half smiled. "It's the happiest I've ever been. And it didn't matter what we were up against. It didn't matter, because I had Gabe, and we loved each other. We made our own little light in the darkness of the life we live, and that made all the crap in the world worth it. Admitting that I loved Gabriel.... It was one of the best things I've ever done, and I will never regret a single second I spent with him. But now he's gone, and that hurts. But if I could go back, I'd do everything exactly the same, because being in love with Gabriel was one of the greatest things to ever happen to me. And you have the chance for that same feeling, Dean. I know you feel that way about Cas, and I KNOW he feels the same way about you. And I don't want you to waste the chance for happiness like what I've had because you're scared of losing him. Take the chance, Dean. Take the stupid chance and be with Cas. I promise you won't regret it."

With that, Sam got up, and walked away, leaving Dean alone with his thoughts.

And Dean took the chance. For the first time in his life, he followed the advice someone had given him.

And Sam was right.

He didn't regret it for a second.