The first time he said it, it was almost a panicked blurt. He hadn't planned it; it just scampered out of his mouth like a frightened animal. The angel had replied with a soft smile simply saying:

"I love you, too, Dean."

He'd felt a huge weight lift from his shoulders. Like he was Atlas and someone had taken his burden. It was incredible how easy it was to suddenly breathe freely and smile openly. But then:

"You are truly the best friend I have ever had."

He felt something similar to a knife stab through his gut at the words. Best friend. Of course. He'd been stupid to think the angel could have meant anything else. It was pure insanity.

"You guys ready to-."

His brother had paused in the doorway, eyes flicking back and forth between the two of them. He'd tried to hide the raw pain that ripped through him, but it was clear that Sam could see it.

"You guys alright?"

His angel had smiled widely, grinning that stupid, innocent grin. He nodded eagerly, seeming to be quite pleased with having forcefully shoved the hunter's heart out through his back.

"Fine, Sam. What is it?"

Sam's eyes bored into his, obviously not believing what he'd said. He glared back at him, daring him to challenge his word. Sam's eyebrows furrowed, but he dropped it. For the moment.

"You ready to go?"

"Ready," he'd muttered, turning to grab his bag.

The second time was pure and unabated lust. He couldn't help it. For some reason the angel had been drenched in water. He was soaked and it made the hunter shiver with want.

"I love you too, of course," Castiel had replied, though he looked rather oblivious, "Have I not said that you are truly the greatest friend I have ever had? Do you need reassurance more often?"

"No, no, it's fine," Dean mumbled, "Just thought I'd reassure you."

He'd laughed nervously and turned away, groping in the dark for some sort of conversation other than the one involving him grabbing the stupid angel and backing him into the nearest wall.

"Why are you wet?" he questioned.

"It was raining where I was before," Castiel answered.

"Right, well, shouldn't you use your mojo to dry yourself?" he suggested.

Castiel looked pleasantly surprised as he looked down at himself. Dean blinked and the angel was dry and smiling. At him. With those plump, gorgeous lips. It was that small smile he barely used that showed approval and appreciation.

"Thank you, Dean," Cas had said, sounding entirely too genuine for something so little.

"Any time," Dean had answered, his voice wobbling from uneasiness, "So…what's the news?"

"Oh, right," Cas said, jumping into the newest news.

Dean paid attention only enough to get the bare minimum, using the rest of his attention to focus on Castiel's perfectness. He knew this wasn't Castiel's true form, but somehow it seemed to fit the angel. The dirty trench coat shifted slightly as Cas took an unconscious step forward. That stupid coat was going to be the death of Dean Winchester, he just knew it.

The third time it was absolute fear and desperation. He stared at his angel with pleading and hope, only to see a broken man before him. His angel's eyes were wide with more fear than Dean was feeling. He only saw panic and brokenness in the Angel of Thursday's face. He wished desperately that he had known that this is what Castiel had meant when he said "shift". He would never have let his sweet guardian do this had he known. Even through the hurt and betrayal Dean had felt, he'd still felt the words as strongly as before. And now there was nothing he could do but drag himself away and reassure Sam that Cas would be alright.

The fourth time he could hear his own depression in his voice. It was a plea for Cas to snap out of it. He hoped that a confession would be enough for Cas to be sane again. It was stupid, he knew that, but he'd hoped that maybe for once his life could be like a fairy tale.

"I love you as well, Dean," Cas answered, that smile that Dean dubbed the "crazy Cas smile" plastered on his face, "You are-."

"Yeah, yeah, best friend ever," Dean interrupted, "I get it."

Cas looked confused but only said:

"Your move."

The fifth time was as he felt his world being ripped to shreds. He could feel everything falling out beneath him. He was being sucked into something else, into something darker. He reached out, begging for his hand to claim what he always wanted. And it landed on the sleeve of his guardian angel. Castiel looked back at him with a pained expression and said something in return. Dean couldn't hear what it was, but it looked suspiciously like:

"I love you too."

The sixth time it was relief. Pure relief in seeing Castiel for the first time in forever that brought the whispered words to his mouth. As he squeezed Cas tight against his chest he breathed the words into the angel's ear hoping beyond all hope that they'd finally make it through his thick skull. But Cas didn't hear him. Dean had been too soft spoken, his words catching on the wind and whipping away to get lost in the trees.

The seventh time it was accompanied with a real, wide grin. It was filled with nervousness and hope. Dean was silently begging for this to be the thing that convinced Castiel to stop pretending he was some normal human being and come home. His eyes pleaded for him to snap out of it as Cas gave his signature soft smile.

"I love you, too, of course I do," Cas said, "You and Sam have been excellent to me. But I just don't think it will work. I'm no good at your life without my powers."

"Right…" Dean trailed off, unsure of how to be any clearer than he already was.

The eighth time was exasperation and annoyance.

"I can't let you do this," he said, one hand gripping the steering wheel tightly.

"Why not?" Castiel asked, innocence dripping from his words.

"Because I love you," Dean ground out, his teeth clenched in frustration.

"I also love you," Cas answered, "I don't understand why this impedes allowing me to go."

"No, you idiot!" Dean shouted, "Like this!"

He reached out, grabbing Cas by his shirt front and yanking him forward. He smacked their lips together, eagerly claiming what was rightfully his. Cas gasped against his lips and let out a tiny groan before softly returning the assault. Dean felt himself relax, as though everything was finally as it should be. He nipped at Cas's sweet lips before pulling away to breathe. He laid his forehead against Castiel's and sighed.

And the ninth time he finally heard what he wanted to hear in response.

"I love you too, Dean."