Dean gets out of the car and makes his way through the snow covered graves until he gets to the one he's looking for. He kneels down to put the flowers on the grave.
"Hey mom. I know you haven't heard from me in a while. A couple years actually. I brought you some flowers. I don't really know much about flowers, so I just picked out whatever looked the nicest.
"There have been some big changes since the last time I was here. Sammy's finally settled down, I don't think I've ever seen him so happy. You would love her mom, she loves him so much and she takes good care of him. Little Sammy's a dad now too! Can you believe it? Seems like just yesterday he was a baby himself and now he's got two of his own. They're the most adorable babies you've ever seen. He named them Mary Elizabeth, and Daniel John. They're 6 months old, and Mary, she looks so much like you. I was just at their house tonight for Christmas dinner. Sammy's done good for himself, mom. He finally got out of the hunting life, he finished school, got the job he always dreamed of, fell in love and started a family. He has the kind of life you always wanted us to have, you would be so proud.
"I've been good. I'm still hunting. I know this isn't the life you wanted for me, but I really don't think there's anything else I could do. I wouldn't be able to stop thinking about all the people that need help, need saving. I know, I know, that isn't my burden to bear. But, I really wouldn't be feel okay doing anything else, and I've been coming back to visit Sammy as much as possible. Sometimes, I'll even stay for a whole week.
"And, well, I haven't been alone. Sammy's not hunting with me any more, but Castiel has been. You remember me telling you about Cas, right? The angel that got me out of hell. Well, since he lost his powers, he's become a hunter. It worked out well actually, Sammy stuck with us until Cas had the hang of it and could take care of himself on a hunt. Then, Sammy got to go live the life he wanted, and I got to keep hunting with Cas.
"I don't even know how to describe Cas. He can actually use cell phone properly now, his appetite rivals mine, he spends most of the time we're driving in the impala sleeping, and he makes jokes that leave me gasping for air. Big difference from the last time I told you about him, eh?
"He has the most beautiful, bright blue eyes, and he doesn't do it often, but, I swear, there's nothing better in the world than his smile. Not even pie, and you remember how much I love pie, don't you? He looks so peaceful and innocent when he's asleep and when he doesn't think I can see, I catch him looking at me like dad used to look at you. He believes in me so much mom, and I'm so scared he's going to realize I'm actually just a monster inside. I'm so scared he's going to realize I'm not worth sticking around for. I'm scared of losing him. I've never been more scared of anything. I … I've never felt anything like this before. Not even with Lisa, not even close. I'm so in love with him, and I just wish you could meet him. I think you would like him. He can take some getting used to, but I've never met anybody who makes me want to try as hard as he does. He's so damn loyal. You should have seen when he was an angel. Anybody made the littlest move against me or Sammy and he would smite them in an instant. Hell, he even turned his back on heaven for us. He's made mistakes, but so have I, and his heart has always been in the right place.
"I don't deserve him, I know I don't. I'm never going to find someone who treats me better than he does. He doesn't let me run away like I always do and he always knows exactly what I need. Sometimes I'm convinced he still has the ability to read minds. Well, I just wanted you to know that I found the person I'm going to spend the rest of my life with. And don't worry about me and Sammy; we're doing alright. Tell dad I said hi okay? I'll be back soon. I promise this time. I love you mom, and I miss you so much".
Dean stays there for a little while, just kneeling in front of the grave. He doesn't want to leave. Coming here hurts, but he needs this. He needs to feel close to his mom, needs her to know that everything is alright and hopes that she's happy with how his and Sammy's lives turned out. Eventually he drags himself away and drives back to the motel where he knows he has someone who will always love him more than he deserves waiting for him.