A/N

Just a quick Destiel oneshot that's been nagging at me ever since I finished season 11 (contains spoilers)

Headfirst for Halos

To some, Dean Winchester may have been the most problematic person on the planet. With his many flaws and failings almost costing the world several times, it was hard to see the good in his actions.

But to others, he was the best human they could have possibly hoped to meet. From the moment he first saw him, Castiel knew he had made the right choice in pulling him up from hell. After all these years, the only thing that had changed between them was the increase in the angel's love for him.

How fitting was it that heaven's most problematic angel was head over heels for earth's most problematic human.

He had learned to bury his feelings though, because from the moment the angel met the hunter, he knew there was nothing but trouble ahead. And how right he was.

They had been through everything together, the two hunters and their wayward angel.

And what wasn't there to love about Dean Winchester? Even if some only saw Dean for his flaws, Castiel knew better. From his loyalty to his swaggering attitude, Dean Winchester was an utterly perfect human. It had destroyed Castiel to watch him suffer through all his trials and hardships, especially when the angel was the cause of these problems.

Over the years, he had his own share of mistakes and troubles to deal with enough to rival even the Winchesters. All he wanted to do was the right thing. No matter how far he went to achieve that, or how twisted his ideals became, that was always the heart of his motivation. Maybe it was because he thought that he could singlehandedly fix everything, but he didn't realize the consequences of his actions. He had become too arrogant in his ways, and it would be his undoing.

Later, when he spent a forever in purgatory with Dean, he thought maybe he could atone for his mistakes by doing everything in his power to shield Dean from the darker horrors of that place. What he wasn't prepared for was Dean's absolute desperation in trying to get them out of there. He had never dreamed that Dean would go to such lengths to save him after all he had done, and it crushed him to push the hunter away. Dean didn't deserve him, and he wouldn't have the hunter going in harm's way for someone as flawed as Castiel.

For all of his flaws, Dean always tried to do the right thing. No matter the situation, no matter the consequences, he was fatally loyal to Sam and Castiel. Again and again, Castiel was shocked by how much Dean cared about him. And maybe he expected too much, but whenever it was just the two of them Castiel would wait for Dean to say something that showed he cared for the angel on a deeper level than just, well, friends.

Here they were again though, and after everything they had been through, Dean was going to do it again. He was going to sacrifice himself for the final time to save the world, and all Castiel could do was sit by and watch. He could only observe as Rowena and Billie aided in building the bomb of souls that was to be Dean himself.

And it almost killed him to stay silent as he watched the hunter in those final hours.

He struggled greater internally with his feelings more than he ever had before. This was the last time he would ever see Dean, and it was his final opportunity to make the move he had been waiting to make since the moment he first saw him.

He was terrified though, because if he did work up the courage to say it, it could completely backfire. What if after everything Dean had done, the small things like shared glances to the big things like sacrificing himself, meant nothing more to him than just what he would do for a friend?

What if it was only him that felt these things, like the twinges of electricity whenever he was alone with Dean? Or maybe it was only him that read into the glances he would sometimes throw his way.

Maybe it was all a figment of his imagination, because how could a human fall in love with someone like him? How could Dean feel anything other than a sense of shared purpose after all Castiel had done wrong?

How could he even hope that this would work out right?

When he had sat in the car with Dean, he thought that maybe he would finally do it. Maybe he would finally tell Dean exactly how he felt about him, and maybe it work out alright. He worked up the nerve, slowly waiting for the right opportunity, choosing his words carefully. The hunter looked perfect in the afternoon light, his eyes fixed intently on the road, a resolute hardness set in his eyes at the path ahead.

But then Dean said the seven words that sent his whole plan crashing down in flames.

"You're like a brother to me, Cas."

The angel had been momentarily stunned at first because he hadn't expected it, and then because it was the exact opposite of where he was hoping this conversation would go. It should have been impossible, but he felt his heart breaking.

Those words should have settled it for him, but it didn't.

The rest of that agonizing day, his stomach had churned with worry and anxiety. He sat, helpless to stop Dean's oncoming death, as the internal battle continued within him.

This was it. His last chance.

He would never see the green eyed hunter again, never see him whether it be in times of strife or happiness. He would never see Dean grow old, or be with the hunter to see the world his sacrifice would create. He would never share another meaning filled glance with him, never another conversation in the Impala. Never again would Castiel see the hunter he loved.

Never again would he have a chance like this.

As they drove to the cemetery where Mary Winchester was buried, Castiel's emotions almost got the best of him several times. Several times he almost just flew away, unable to cope with the crushing sorrow inside of him. Never had he felt sadness like this, and as he glanced over he felt for Sam, who must also be feeling it.

When they stood by the Impala, he stared at the back of Dean's jacket, trying to ignore the pulsating powerful aura of souls around him that signified his impending death. He tried to remember that this was a good thing; that if Dean could choose how he were to die it would be like this. He desperately held onto the good things, like the way Dean had helped him while he was human, and the constant stream of prayers the hunter sent his way.

In truth though, remembering those prayers was almost the saddest part for Castiel. Although he had told no one else, Dean prayed almost every night to Castiel. Most of the time it was just a 'hello, hope you're okay,' prayer, but sometimes when he was in trouble, it deeper and more meaningful. And he always heard it, even if he couldn't answer it. The angel thought that at this point, he probably knew Dean better than Sam.

He saw the resoluteness in the hunter's squared shoulders as he turned from the grave and marched solemnly back to the car with Sam. He said his 'thank you's' and 'goodbyes' to the others gathered first, saving Castiel and his brother for last.

The moment Dean turned to him, the angel gave up on his internal battle. The moment his eyes met the hunter's green ones, he melted.

This was it.

This was goodbye.

And there would never be another chance like this.

Castiel had been called many things in his long life, everything ranging from 'savior' to 'abomination.' But if there was one thing he didn't want to be remembered as, it was a coward.

His melted insides solidified suddenly, and he looked at Dean with a new resoluteness he had never felt before.

This was it—the goodbye to end all goodbyes.

And he sure as hell wasn't backing down this time.

There had never been a moment as perfect as this, and he forced his eyes to stay locked on Dean's, remembering everything he loved about the hunter, pulling all the suppressed emotion out from the back of his mind and letting it flow through him, feeling everything he had forbidden himself to feel.

Heaven's most problematic angel was in love with Earth's most problematic human, and he didn't care who knew it.

This time he made the first step forward, staring at Dean and letting all his emotion shine through. He saw the hunter look confused, but at this point there was no going back. He was going to give Dean the goodbye he deserved.

He took another step, and there was only a few inches between them now. The rest of them had gone silent, but Castiel forgot they were even there. Dean's breath stopped, and he looked questioningly at the angel.

The angel answered the question in the most direct way possible. Forgetting any possibility that this could completely backfire, he reached across the space between them and grabbed Dean's jacket with both hands, closing the space between them.

The kiss was quick though, quicker than he wanted, because Dean was so startled that he pulled away before Castiel could react. The hunter stepped back, looked flustered and sputtering. The angel froze, waiting for the hunter's reaction.

"I—I…."

An apology was in his throat now, and his face was turning red. All of his doubts and fears suddenly resurfaced. How could he do something so stupid? He had ruined it, ruined everything—

"Thanks, Cas."

And this time it was Dean who pulled Castiel in, and kissed him like there was no tomorrow. It was everything the angel had imagined and more. He could have sworn that every spark of energy inside of him was exploding simultaneously as the hunter held him close, keeping them connected.

When Dean finally pulled away, Castiel was in such a state of bliss and happiness that he didn't know what to do. He tore his gaze from the hunter and slid to the rest of the crowd currently watching them. Dean turned, and he sheepishly met his brother's eyes.

Everyone was shocked silent, but Sam broke it with a barking laugh. His face broke out into a smile and all pain was suddenly erased from his features as he looked between the angel and the hunter. He ran over to Castiel and hugged him, still laughing.

"Finally Cas! If I had to see you two stare at each other like that one more time I swear I was going to go crazy!"

Castiel was still shocked, and finally he was unable to hold the smile within him back. Sam pulled away to clap Dean on the back and the angel saw the rest of the faces around him, including well, God himself.

Oh—he had forgotten about Chuck.

Rowena looked utterly baffled, and she glanced from Chuck to Dean, and then to Castiel.

"What in the name of—what the hell was that all about?" she looked to Chuck, still bewildered.

Chuck looked the most unaffected by the turn of events. "You didn't see that coming?"

Rowena looked even more shocked. "You did?"

"Oh I could see that coming from about two miles away," he answered Rowena with a smile.

Castiel laughed nervously, and looked at Dean, who locked eyes with him for a second. Where pain and sadness had been previously etched there was now light and a slight dazedness.

"You know what this means?" Sam asked, a smile still shining on his face.

"I'm not as straight as I thought?" Dean answered with a bemused expression.

"Well I kind of always assumed that," Sam answered, "Now, though, Crowley owes me ten bucks!"

Dean shook his head, not even trying to comprehend what Sam was implying. He looked at his brother with a new appreciation, and for the last time, stepped in to embrace him. They both looked a mixture of emotions that Castiel couldn't even hope to untangle, but he knew that in that moment of darkness, he had conquered what he feared most and come out on top.

When they pulled apart, Dean looked at Cas one last time, and finally, finally, Castiel saw all the emotion that the hunter had been afraid to show displayed on his face, and he knew that though they may have been through hell and back, (literally) they had ended on the best note possible.

A mixture of leftover sadness and the return of the stoic resoluteness replaced the softness of the final glance he had thrown the angel's way. He looked to Chuck, who glanced one more time between them. For a moment Castiel thought he saw the sadness he had felt earlier reflected in Chuck's eyes, like it was killing him to have to do this. Then he snapped.

Just like that, Dean was gone.

The happiness faded from the angel's expression, and he felt a stone drop in his stomach.

No.

There was no way he could have prepared for this moment, no way to process what had happened. Nothing but shock and sadness left to replace the sudden burst of happiness.

He had done it, but now Dean was gone.

A quiet 'I love you' was still caught in his throat.