Tonight he drinks. He has done this every year since he was old enough to know what the alcohol would do to you, even if he had to hide it from his father. He didn't have to hide it much, because his father always did the same thing on this night every year.
Tonight he drinks and drinks to get as drunk as he possibly can so the pain will stop. This year there's not just the pain of his mother's death, but of his fathers as well.
Tonight was the night his childhood ended and he became the protector instead of the big brother. Tonight was the night he lost his mother all those many years ago. He guesses that, in a sense, he lost his father on that night as well, because from then on he became obsessed with the hunt and wasn't much of a father anymore.
Tonight he drinks. He never used to drink on this night and never had a reason to, except for that one shot of Tequila as a toast to the woman he barely even knew. Even this was only something he started when he was at college.
Tonight he drinks. It's the first time in a long time that he gets really, really drunk. The first time in a year. He drinks trying, hoping, to forget. To forget her, forget the things he's done in the past year.
Tonight was the night he lost his true love. The nightmares of her on the ceiling haunted him for weeks, months, after. Tonight was also the night he lost his mother, but he doesn't remember her. So he has his one shot in her memory and then downs beer after beer to forget the other woman in his life taken on this night.
Tonight they drink. They drink carrying on the annual Winchester tradition. There's no one around this time to hide the bottles from or the smell of alcohol on their breaths and there's no one there to tell them not to.
Tonight they drink. For the women they loved who are now gone. One drinks to drown pain and one drinks to drown memories, but for the first time they have a reason to drink together. And so they do.
Tonight many years ago, they both lost their mother. One can remember her and he wishes beyond all hope that he didn't, while the other wishes beyond all hope that he could have just one concrete memory of her. But then he thinks of the memories he has of his lost lover, and realizes that having that one memory would only make him want to forget it, like his brother does.
