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There is a plot and timeline to these drabbles, trust me. Currently, they are set in season 5 and then there will be a massive time jump and it will continue from there.
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4. Failure
"Dean? What's wrong?" Castiel said. Dean was leaning against the hood of the Impala outside Bobby Singer's house with a bottle of beer in his hand and a troubled look on his face.
"Nothing, Cas," he said, taking a drink. Castiel simply continued to stare at him. That wasn't true. He wasn't reading Dean's mind but he could still sense the troubled thoughts and feelings swirling around inside the human.
"Don't lie to me, Dean." Castiel stepped forward so that he and Dean were almost touching. "I know that something is wrong. Tell me."
"Why do you care?" Dean muttered. "You're a perfect little angel. Me? I'm a failure. Always have been, always will be."
Castiel frowned, his head cocked to the side in confusion. He was not perfect! And Dean was not a failure! Why would he think this?
"Dean," he said.
"Don't," Dean interrupted. "I don't need to hear any of your crap about how I'm the Righteous Man and I'm not a failure and blah, blah, blah. Sam may've busted Lucifer out of the Cage but it's my fault he could even do that in the first place. All this crap that's happening is on me!"
"Dean!" Castiel said sharply. Dean looked at him, the green eyes that Castiel found to be one of the most beautiful things in the world filled with pain and self-loathing. Castiel felt pity and confusion. Did Dean really think that little of himself?
"You are not a failure." Castiel put a hand on Dean's shoulder. The man tensed but didn't pull away. Castiel looked deep into his eyes to emphasise his words – after all, the eyes were the windows to the soul. "Any other man would have also broken in your place."
"Dad didn't," Dean said bitterly. "He held out for a hundred years. I broke after thirty! And you know what?" His voice dropped to a whisper and he looked down. "I liked it. I enjoyed torturing those souls. That makes me a monster, Cas. I'm no better than any of them down in the Pit."
Castiel's pity for Dean grew.
"You are flawed," he said firmly. "You are a flawed human being. But you are not a failure. You make mistakes but you are not a failure of a person. You are simply a person. Eventually, had he not been able to escape, John would have succumbed. Everybody does. Do not think any less of yourself for breaking!"
Castiel realised that his voice had grown louder and more powerful and commanding throughout his speech. Dean was still staring at him but this time Castiel could sense gratitude and even hope!
"And I am not perfect," Castiel continued in a mutter. "I have also made mistakes. I did not tell you about Lilith until it was too late to stop Sam. I freed Sam to allow him to kill Lilith. I am also to blame for Lucifer's release. You don't need to take all of the blame onto your shoulders, Dean."
Dean gave Castiel a small smile but to the angel that was the equivalent of a hug.
"I'll just finish this off," Dean said, gesturing to his beer. "I'll be back inside soon."
"I will meet you there," Castiel said. He turned and was about to walk away when Dean called his name. He turned back to face Dean.
"Thanks, Cas," Dean said. "I needed that kick up the ass, didn't I?"
Castiel was confused. He had not kicked Dean up the bottom! But Dean seemed to be happy, so he simply favoured him with a small smile.
"You did," Castiel said. "But that is – what is the saying? That is what friends are for."