Castiel wasn't exactly the brightest angel out there. So he was confused when one night he had to stay at a hotel with the Winchesters and only Sam had come back from their hunt.

"Oh, Hey Cas!"

"Sam, I noticed your brother is not with you. Is he alright?"

"Uh, yeah Cas, he's fine… He'll be back later. Don't worry about it." Sam told him in an almost forced voice, but of course Castiel didn't catch this, and so when Dean finally got back, Castiel was there to greet him.

"Hello Dean."

"Uh, hey Cas. How's it going?"

"Never mind that Dean, why were you gone so long? Is something wrong?" And then that was when Castiel would see the regret and the shame in his eyes.

"It was nothing, Cas. I need to get some sleep man, it's late. I'll see you in the morning, okay?" And Castiel would reply with 'I'll watch over you Dean', to which he would reply with 'Hell No!', and Castiel would just be left alone to think.

.~~~.

The next time Dean didn't come back, Castiel questioned Sam more thoroughly.

"Sam, where is Dean?"

"He's Nowhere, Cas."

"Stop lying to me Sam. You wouldn't give me a straight answer last time, and I'm just concerned for your brother's safety."

"Look, Cas. I don't really think it's that important, and-"

"Sam."

"…Fine. Alright, look. Dean isn't really a guy of good morals. He… uh, went home with a girl. I… I think it's just kind of his way of coping with things, honestly."

"Oh…"

"You… You do know what I mean, right?"

"Yes, Sam."

And Castiel said nothing else, but still waited once more for Dean to come back. When he did, Castiel was not the first to speak.

"Oh, Cas? It's really late, man. Why are you still here?"

"…"

"Cas? You hearing me buddy?"

"Yes Dean. I'm just glad you are okay, that's all."

"Well thanks, Cas. Didn't know you cared." Dean scoffed, but Castiel wasn't one to get his sarcasm.

"Of course I do. Both Sam and I care for you."

"…Dude, it was just a joke." He responded, letting out an uncomfortable laugh and occupying himself by taking his jacket off and throwing it carelessly on the counter.

"Oh, Right."

"Yeah, okay, well... Night Cas."

And then Castiel didn't respond, and he stood next to Dean's jacket with a dull sadness lingering over him.

.~~~.

This time, it was different.

Dean was smirking to himself as he entered the place he currently referred to as "Home", but was surprised to see that Castiel was there.

"Cas? When did you get here?"

"Dean," Castiel said, ignoring the question, "I don't understand how you find any kind of "fulfillment" in these little act's you partake in."

Dean stood there silently, trying to find the words he would respond with.

"Well, I don't think I-"

"I hate this feeling I get. Whenever you're with one of them…" Castiel mumbled. "I want to help…"

"Look, Cas. I don't need any "help", okay? There's nothing wrong." He replied angrily, but he couldn't shake the guilty feeling that he was getting, and it seemed to be engulfing his senses.

"You're wrong. I had to put you back together piece by piece in Hell, Dean. I know more about you than you think, and I know humans have a tendency to cover up their feeling with things such as alcohol and se-"

"Well you know what? News flash, Cas, there are a lot of problems in my life! There are a lot of problems with me! I just don't get why-"

"Am I a problem?" Castiel asked, his gaze to the ground.

"What?"

"Am I a problem, Dean?"

Dean scoffed defensively. "No, you aren't a-"

"Then why…" Castiel said, looking up at Dean, who swore the angel was going to cry then and there, "why can't I be the one to take your problems away? Why can't I be the one to listen? I've done so much for you! I always come when you call. I put my grace on the line for you constantly! Do you think I would care? Wouldn't listen?

Dean shook his head, letting out a defensive laugh. "Cas, no… It's just that-"

"Just that what, Dean? Can you tell me why I feel this way?"

"Look, I… I know how you feel. But this. We both know that this can't work out… I can't-"

"Dean..."

"We need to drop this."

Castiel just nodded, and Dean's frown could have reached to his neck.

"Goodbye, Dean."

"…I'm sorry, Cas."

"Me too."

And that was the last time. And every other time, Castiel would try not to think about how much it hurt.