A Birthday/Deathday Drink
At first it was about like this. Once a year, every year, Dean would go find a bar, classier than his usual haunts, sit down, and order two drinks. One he would slowly work through as the night passed and the other would just sit next to him, sweating on a napkin. When he was approached, as was inevitable, he would simply say he already had company, thank you, and turn back to his mostly empty glass and the watered down drink beside him.
When closing time would draw near, he would pick himself up off his stool, drink long finished, throw some money down on the bar, and mutter a simple, "Happy birthday, Mom." This was the tradition he had begun so very long ago.
Dean took to going out for a drink for all the people he loved and met and knew that died. He tried to go at least once every year for that person, especially on their birthday, just his mom at first, but then came his father, Bobby, Ellen, Jo, Ash, Kevin, and the list never seemed to stop.
So eventually it came to this. Dean sitting in a bar, holding his fourth, possibly sixth whiskey of the evening, not even bothering to respond if someone came up to him. That is however until Cas sat down next to him.
Earlier that evening, when Dean has grabbed his coat and slammed the bunker door shut, Cas had just looked after him rather confusedly. Sam, knowing Castiel's curiosity would get the better of him, warned him not to follow Dean when he was in a mood like this. Sam told him that Dean would come back later, smelling strongly of alcohol but in a calmer mood. Not happier, necessarily, just calmer. Cas, of course, then proceeded to ignore every word Sam said and followed Dean.
"Cas. Unless you have the best of Jack Daniels hidden under that coat of yours, I'm not in the mood."
"I… do not who this man Jack Daniels it is you speak of or why he would be hiding in my coat, but I only wanted to tell you of your family."
"My family? Cas, what do you know about my family? Do you know that they seem to be the world's best cannon fodder? Or that, even if I haven't met them, anywhere Sam and I go, we carry around a giant blood soaked target with us. Anvil hits the spot every time."
"No, Dean. I wanted to tell you of their lives. Their lives in heaven."