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All the Times I Loved You

Summary:

“Wait. You were jealous? Of Crowley?!” Dean clutched at his stomach as he doubled over in his chair, laughter echoing throughout the room.

“Are you done?” Cas finally muttered, heat visibly rising to his cheeks. He was finally looking in Dean’s direction, though no less crabby.

“Not even close,” Dean replied as he wiped a tear away from his eye.

-

Cas and Dean tell one another how long they’ve been in love with each other.

Notes:

Cas and Dean sit down and talk about their history.

In which Dean is way too smug, and Cas loves this idiot.

(See the end of the work for more notes.)

Work Text:

“Wait. You were jealous? Of Crowley?!”

Castiel looked away sheepishly, rolling his eyes. They landed on the weathered bookcase in the corner of the room. It was littered with disorganised files and books that the bunker residents had let get out of hand. He glared at it as if the piece of furniture had asked the offending question.

Dean clutched at his stomach as he doubled over in his chair, laughter echoing throughout the room. He glanced up at Cas when he finally began to regain composure.

However, the angel’s expression had Dean immediately falling apart again. The howling continued on for another stretch of time. He gripped onto the cotton of his shirt tightly, attempting to push down the ache that was now developing in his stomach from laughing.

“Are you done?” Cas finally muttered, heat visibly rising to his cheeks. He was finally looking in Dean’s direction, though no less crabby.

“Not even close,” Dean replied as he wiped a tear away from his eye. But as he responded he finally straightened up to look at Cas. Dean’s smug grin only further engraved the frown on the other man’s face. But he still couldn’t help a remaining chuckle or two continue to escape him.

“Oh come on, it’s pretty funny.”

“Not really.” The frown had transformed into a pout of sorts.

Dean couldn’t help but grin again, this time more so at how adorable Cas looked. Like a grumpy teddy bear, he thought to himself.

“Okay well, if it makes you feel better-” He began, trying to catch Cas’ eye. Cas didn’t waver, opting to look pointedly at the wall behind Dean.

“I was pretty jealous when you went on that date with your manager.” Dean offered, his voice quieting slightly as he made the admission.

Cas’ eyes finally shifted to Dean, he tilted his head. His voice was cautious and defensive as he replied.

“Really?”

“Yeah, man. I didn’t want you to go.” Dean huffed out a chuckle, but it was forced. He felt self-conscious admitting it.

“But, you encouraged me.” Cas frowned this time in confusion. His statement sounded like a question. A familiar head tilt framed his befuddlement.

“Yeah, well I wanted to be a good friend. Also, my head was still pretty far up my ass at the time, so I don’t think I even knew I was jealous.” He countered.

Dean still remembered the wrongness he felt in that moment. Dropping Cas off at Nora’s place. How he wanted to stop him but he didn’t understand why, and so opted instead for exaggerated enthusiasm. As he contemplated what he would’ve said if he hadn’t chickened out in the car that night, his thoughts were interrupted.

“It was very far up there.” Castiel’s face finally had a hint of a smile on it.

It was Dean’s turn to roll his eyes this time, though he couldn’t keep the lightness out of the action.

“We were really clueless,” Dean muttered. Shaking his head with a smile, though there was a sadness behind his eyes as he spoke. Cas, as perceptive as ever to Dean, picked up on it.

He squinted slightly in question.

Dean shook his head. “It’s nothing. It’s just-“ He sighed. “Imagine if we’d just sorted our shit out sooner. Before your Empty deal, before Chuck, before everything. We could’ve had this-”

He gestured between them. “Had this ages ago.”

Cas smiled softly. “I’m glad to have it at all Dean, I never even let myself hope that it could be possible. That you could love me.”

That stunned Dean into silence for a moment.

The silence lingered, but it was peaceful. They both simmered in the aftermath of Castiel’s words and the elation of now having what they once thought wasn’t possible.

Finally, when the emotion prickling at Dean’s eyes started to get dangerously noticeable, he coughed.

“So. What other times were you secretly in love with me?” He smirked at Castiel, raising his eyebrows.

There was an incredulous pause.

“You’ve ruined the moment Dean.” Castiel deadpanned back, his eyes flicking up to the ceiling in exaggerated frustration.

“Oh come on.” Dean jokingly whined.

“No.”

“Please?”

Cas sighed dramatically.

“Okay fine. But if I must, then you have to as well.” He raised his brows tauntingly, waiting for Dean to drop the matter.

Instead, Dean narrowed his eyes in challenge. “Fine.”

“You go first,” Cas responded.

“Not fair, I said the last one.” He shook his head, grabbing his forgotten beer bottle off of the table and taking a sip. He had to admit, he was extremely curious to see where this would go.

“Fine.” Cas paused, wracking through his brain for a moment. He finally seemed to land on an example, as his demeanour changed. He straightened up slightly, glancing around the room and taking in a breath.

“Well, I may as well start at the beginning.” He stated plainly. “When I rebelled for you before the final seal was broken. I was in love with you then.” He glanced around the room casually, though it was clear the admission was anything but casual.

Silence cut through the air again. It was not where either of them had expected the conversation to go. Or start at least.

Dean sat somewhat frozen, overwhelmed. That had been so early on.

Much to his disapproval, his eyes welled up slightly as he attempted to think of a response to the confession.

“Your turn.” Cas quickly cut in as Dean opened his mouth.

He decided to let it go for now. He’d need longer to fully process what Cas had said anyway, to respond in a way worthy of what Cas deserved.

Dean pondered for a moment before he expressed the first instance that came to mind.

“When you walked into that lake- with the Leviathan. I didn’t realise it then but, yeah I was- You know.” He looked down quickly. It wasn’t a good memory.

Cas’ face was equal parts remorseful and reverent. “Even after I-“

“Yeah. I think- I think that’s what made it hurt more.” The guilt which flashed across the angel’s face had Dean continuing on in a hurry.

“Hey, don’t. I forgave you for that years ago. And I’ve said and done a lot worse since then- I’m just saying- It’s fine.” They shared another look, comforting each other with unsaid words.

“My turn then,” Castiel responded when he was ready.

“Pick another fun one like the Crowley thing.” Dean cut in. He received a glare that had him chuckling.

“Well, I don’t know if this is fun, necessarily, but purgatory.”

“Me too.”

“You can’t steal mine.” Cas narrowed his eyes at Dean, though the humour behind them was apparent. That elicited a chuckle from Dean which had Cas clearly preening.

Dean thought again for a moment, not wanting to give another answer that would bring back painful memories for Cas. For either of them.

Finally, he smiled.

“When I gave you that mixtape.”

“The mixtape?” Castiel questioned with a squint.

He hadn’t considered he’d have to explain its significance to Cas, something which in hindsight, had him sweating slightly.

“Yeah it uh- Usually when you give a mixtape like that to someone it’s- You know.” He muttered, flushing. He still wasn’t great with all this.

“I don’t know actually.”

At first, Dean bought Cas’ pondering expression. But then he noticed the corners of his mouth tilting upwards, and shot him a glare.

“Whatever, your turn.”

“No, you need to explain the mixtape, Dean.” Cas replied, feigning a serious tone. He was great at turning on that oblivious angel act when he wanted to, despite having been on Earth for years now.

Dean glanced side to side with a huff. “You know! It’s like in those chick-flicks-“

“That you love.”

“Yeah, yeah. But you’ve seen them it’s-“ Dean attempted to sputter out an end to the sentence but it did not come.

He was still having trouble with all the- feelings- stuff. Telling Cas he loved him? Yeah sure, he’d finally been able to do that. Losing him again had drawn that out of Dean. But at any given moment he was still waiting for the other shoe to drop.

Happiness wasn’t something he was used to keeping for long. Not only that, but he was still unlearning so much. Not cutting himself off right before he said something vulnerable. Not flinching for a moment, every time Cas reached for his hand.

It wasn’t easy.

He blinked rapidly, thinking it over.

“Romantic?” Cas finally offered with a small smile.

Dean blushed. “Yeah. That. Your turn.”

Cas shook his head fondly at Dean before continuing.

“When you took me to that brothel.”

Dean snapped out of his embarrassment and looked up with pinched brows.

“That’s a weird one.”

Cas glanced around with too-casual indifference. Pursing his lips uncharacteristically.

“I’m just saying. I thought the night was going to go much differently when you made the comment about not letting me die a v-“

“Oh!”

Cas looked at Dean knowingly.

“You mean? You wanted to- I- Oh.” Dean blinked blankly at the space before him.

He hadn’t realised that had even been a possibility at the time. He replayed that nights events in his head and then considered how they could’ve gone differently. He was sure he was blushing, which was quite the feat as all his blood seemed to be rushing elsewhere.

“Your turn.” Cas snapped him out of his thoughts. His smirk made it clear he knew the effect his prior words had.

Taking a moment to recover, Dean finally cleared his throat and began to ponder.

He again attempted to search out a happy memory, but with their lives, it was tough to do so.

He sighed, landing on something that at least wouldn’t cause Cas guilt.

“When Lucifer killed you. The night Jack was born.” He gulped, remembering the weight of the pain. “It was- I was a wreck man. I’m pretty sure everyone around me knew- knew why.”

Cas’ brows pinched together, his expression slightly surprised.

“Yeah I wanted to- I was ready to give up after that.” Dean looked away as he said it, not wanting to see the expression on Cas’ face. “I was gonna let myself die.”

Cas’ intake of breath pierced through him. He could hear the pain in that one sound alone.

“I didn’t realise you- I didn’t realise it affected you so badly.” Cas’ voice sounded raspier than usual, his eyes pooled.

“I didn’t tell you. I should’ve told you. Every time you left- were gone-“ Dean’s voice broke slightly. “I was falling apart. Hell, ask Sammy, he had to carry my sorry ass through it.”

Swiftly, as the other man’s exterior began to waver, Cas stood up from his end of the table, moving over to the seat next to Dean. He placed a hand gently on his cheek. It was immediately covered by Dean’s. They let the silence linger for a moment.

Finally, their hands fell, clasping each other in the space between them. Dean gestured for Cas to speak.

“My turn again. In purgatory-“ Cas began.

“You already said that one. Are you out of ideas already? I’m a little insulted buddy-“ Despite a sniffle, the humour began to return to his tone, his lips quirked up slightly.

“In purgatory.” Cas cut back in forcefully. “I was jealous of Benny.” He huffed, turning his head up slightly with a pout.

After a quick moment of surprise Dean’s full-blown smirk properly returned. Cas rolled his eyes again, this time less so annoyed as if he’d intended to gain that reaction.

“Okay, that one might have been justified,” Dean muttered sheepishly, unable to keep the abashed smile off his face.

Castiel narrowed his eyes.

“Oh come on, I’m just kidding…” Cas’ ominous eye squint had him continuing. “Okay, not really- But you have me now don’t you?” Dean reasoned, raising his brows. He squeezed Cas’ hand lightly. His smirk softened to something more tender.

Cas smiled to himself, dropping to a neutral expression as he glanced up at Dean again. “Your turn.”

“I was jealous of Meg,” Dean responded instantly.

Cas hummed lightly in acknowledgement, before immediately countering with a tilt of his head.

“I was jealous of Anna.”

Dean frowned for a moment, then shrugged as if to say ‘fair enough'. That was definitely early on, and knowing that even back then Cas cared about him in that way- he couldn’t think too hard about it.

Realising it was his turn he wracked his brain again, his face pinched in concentration.

“Uh,” He faltered, still unable to land on something.

“Are you out of ideas already? I’m a little insulted Dean.” Cas deadpanned, imitating Dean’s previous gripe. At that, Dean decided to give him a taste of his own medicine from earlier.

After all, it wasn’t fair that Cas kept getting him all flustered.

“Calm down buddy. I got one.” He smiled, dropping his head to disguise the blush that was surely creeping up his cheeks. “I uh- The-” He attempted to stifle the grin appearing on his face.

Cas quirked a brow which really wasn’t helping.

“When you got back from the Empty- the first time around- uh yeah.” He quickly finished, discarding his plan and sticking with a safe answer.

“What was that about?” Cas questioned, narrowing his eyes in suspicion.

“What was what about?”

“Dean.”

“Fine, fine.” Dean glanced around sheepishly. “I uh. I was just remembering you in the cowboy hat.” He swallowed. “I liked it. It, um. You looked good.”

He was certain he was probably beet red at that moment. Cas’ gaze on him definitely wasn’t throwing him any less off balance.

Damn it. It was supposed to be the other way around.

Cas’ eyes narrowed, a curious glimmer behind them. The faintest smile played at the edges of his lips.

“I should’ve kept it.” He smiled knowingly as if he could read Dean’s mind. Deciding to spare him from a complete breakdown if they went any further down the cowboy conversation, Cas continued.

“It’s my turn again. Though I can’t think of more people I was jealous of, so the rest of these won’t be as fun for you.”

Dean chuckled lightly, shaking his head fondly. He then pondered for a moment before responding. “What about Lisa?” He raised a brow.

Cas tilted his head in thought.

“No- I don’t think so. Maybe the life you had together though.”

Dean’s eyes widened slightly. ‘What? The white picket fence life? That’s- that’s something you want?” There was a hopeful tilt to the end of that sentence that didn’t seem to go unnoticed by Cas. Dean cursed himself internally for that.

“At the time... not necessarily.” He paused as if to consider it. “It was more so about the very humanness of it. I didn’t think I could have that… among other things” He looked over at Dean softly with that, only to receive an equally tender look in return.

“But now? Maybe.”

“So what- you’d give up- this-” Dean gestured around the bunker vaguely. “And settle down into something…” He seemed to not know where to go with the rest of the sentence.

“More peaceful?” Cas offered.

And yeah. Dean thought to himself. That was it.

He’d been thinking about it for years now. Though not necessarily allowing himself to factor Cas into the equation. But he had been toying with the idea of what retirement would be like for a while. Of finding some peace eventually.

He realised Cas was still waiting for a response.

“Yeah. More peaceful. Quieter.”

“If you were there. Then yes.”

They looked at each for a moment, an unsaid conversation passing between them. Anywhere the other one was they’d go. Their home was together now. It had been for a while. But now they both knew the other felt the same.

Excitement fluttered in Dean’s chest. He smiled lightly to himself before looking up at Cas again. “It’s still your turn, you know.”

Cas rolled his eyes, making it a full-body event somehow. “Are we really still doing this?”

“Hey!” Dean replied in mock outrage. “I thought you were having fun.”

He received a side-eye in return. “I am. But this is also clearly just boosting your ego to dangerous extents Dean.”

Dean smirked at him. When Cas’ expression didn’t falter, he opted for a pout instead. Sam wasn’t the only one with puppy dog eyes after all. He knew it had worked when the corners of Cas’ lips began tilting upwards.

“Right now,” Cas finally stated.

“Huh?”

“In this moment. In all the mundane moments like this we’ve had and are going to have. I love you.” He didn’t smile, but as he spoke his eyes grew warmer.

Dean’s exaggerated smirk faded away, his brows pinched together and his mouth parted slightly. He blinked a few times as he looked away to the side. He was quiet for a moment.

“Are you okay Dean?”

Dean looked up again, his eyes clearly slightly wet. “You really just say-” He cut himself off with something between a chuckle and a sob. “I love you too.”

Then he added on softly “So much. I-” He shook his head, attempting to compose himself slightly. At that Cas reached over and stroked his face for a moment. His fingers grazed Dean’s hair as his thumb stroked his cheek. After a moment he let it drop again.

As the moment passed Dean wiped a hand over his eyes quickly. “Argh. Enough of that.” He cleared his throat. “Now tell me. Were you serious about retiring?”

Cas smiled at him knowingly. “Are we not listing moments I was in love with you anymore?” He raised a brow.

“We’re taking a break.”

“Yes.”

“Yes?”

“Yes, I was serious about retiring. But only if it’s together.” Cas gazed at him intently, as if trying to decipher where Dean was going with the conversation after this. Or perhaps, trying to seem that way; subduing his hopes so that they wouldn't be painted across his face too blatantly.

Dean nodded. “Okay. Well then. I guess we gotta start house hunting.”

Cas’ brows jumped up all of a sudden. “You’re ready to leave the bunker?” He questioned. “What about Sam?”

“Sam’s fine he- he’s got his own life now. And I uh- I want us to have something of our own.” He smiled wistfully before continuing.

“So whadya say?” He beamed at the man before him.

Cas pondered for a moment, before scrunching his face into an expression of exaggerated concentration. “I have a condition.”

His tone was solemn.

“You have a condition?” Dean asked, slightly incredulous, his brows raised. He had been expecting an instant yes and an excited Cas. Not so much a negotiation. He grew slightly nervous, wondering what the condition could be.

“I want somewhere with room for a garden and animals.” Cas smiled up at him expectantly.

Dean sighed, looking off to the side in mock annoyance. “Already a pain in my ass and we haven’t even moved in together yet.”

“Dean, we already live together.”

“Yeah I know that but- okay yeah whatever- you can have your damn garden and animals.” He huffed out. The annoyed sound was counteracted by the smile on his face. “Now do you agree?”

“I agree.”

A thought struck him. He had agreed to that way too easily. “Wait. What kind of animals are we talking?”

“You’ll see.”

Dean eyed him warily, growing immediately concerned with the too innocent expression he received in response. He sighed, deciding to let it go for the time being.

“Okay now let’s get back to listing our moments.”

“Dean.”

“Cas.”

“Fine- I believe it was your turn.”

“Was it?”

“Dean.”

Notes:

Hope yall enjoyed this. I just couldn't stop thinking about how long these fools have been in love and not even realised it.

xx

If you enjoyed this you should check out Too Old For This for more destiel introspection and retiring