Disclaimer- Since Eric Kripke is not a teenage girl and since I'm not a middle aged man, don't get the right to the show, only the real Eric Kripke does.
It's been six weeks since Cas was killed by the leviathans and Dean has been feeling for and more numb with each passing day. And the only thing Dean can do is drink until he forgets about the pain of Cas' death, for a short while. Ever since that fateful day, Dean has come to the painful realization that he loved Castiel, an Angel of the Lord. IT hurt even more to know that it took Castiel's death for Dean to realize his feelings. The only thing Dean can do it drink until he falls asleep and that is where je sees Cas and every time he wakes up, he forgets for a moment that Cas is dead and Dean will never see him again and that causes Dean to tear up and drink to drown his sorrows.
Finally one night Dean couldn't take it anymore, he had to get out of the motel room. So he quietly grabbed Baby's keys, a bottle of Jack Daniels and drove until there was nothing around but tress and some animals.
"Why did you have to work with Crowley, you know that it wouldn't end well, if Crowley was involved." Dean said out loud as he took a long swig form the bottle, while looking up at the stars.
"Why didn't you listen to me and talk to us instead of ignoring us!" Dean shouted as he took another swig from the bottle.
Before Dean knew what was happening, tears started to stream done his face and where was nothing he could do to stop them.
"Dammit, Cas, why didn't you listen to me and I could have helped you!" Dean screamed to the sky and the bottle fell out of his hands and onto the ground where it shattered and the contents spilled onto the dirt.
When Dean realized that his bottle was destroyed, he decided that he's been outside long enough, but he couldn't bring himself to leave. It was so perfect and it was the only place where he could think about Cas and not have his brother or Bobby looking over his shoulder, making sure that he was ok.
Eventually Dean slide to the ground and leaned against his Baby's hood. He looked up to the stars deep in thought, mainly thinking about his angel and how he wishes that he could talk to Cas and be able to hold him in his arms and tell Cas that he loves him so very much
Suddenly Dean felt something touch his face gently and when Dean opened his eyes. He saw a slick black feather that was so dark that it looked blue and about a foot in length.
With that in hand, Dean knew that he would never be alone again, because he had his angel looking out for him and telling him that he will always watch over Dean.