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Day 1: Dear Sam, They finally locked me up today. Seems like it has been ages since we were fighting the apocalypse or looking for Dad. They think I am crazy, if only they knew. I miss you and Cas. I hear Cas all the time. Well I don't "hear" him. It's more like a whining noise that is distinctive to him. I heard it first when I first got out of hell. The white coats give me medication for it but all it does is make me tired. Sam please come get me. I need a drink and there is a no drink policy here. I can't take it. Come soon.
~Dean
Day 7: Dear Sam, You must not have gotten my last letter cause I am still here. Hell, they might have confiscated it, who knows. The sound is getting louder since they switched my medication. God, I wish Cas was here. He could make it go away. The new medication won't let me sleep. I liked the other pills. Please come get me soon, I really need a drink.
~Dean
Day 14: Dear Sam, Went to see a shrink today. I wasn't paying much attention. The new medication makes me shaky. When will they get the pills right. Anyway the shrink asked about a lot of things. You, Dad, Mom. I asked what they think is wrong with me. They think I am schizophrenic. That is bullshit and we both know it. Every time I brought you up he gave me a weird look. Like he knows something I don't. Please come get me soon, I really need a drink.
~ Dean
Day 60: Dear Sam, Wow 60 days in this place. I think I preferred hell. Where are you Sam? It has been 2 months and nothing. Do you believe them? Do you think I am crazy? Well fuck you Sam. I am fine, I just need a drink. Please get off your high horse and come get me.
~Dean
Day 100: Sam, Please. I need you. The meds stopped doing anything. I am so alone. Please, Cas, Sam, anyone! ~Dean Day 150: Sam, Lisa came to visit me today. First time I've cried since Bobby. She was just as beautiful as always. I asked if she had heard from you. She just frowned and said nothing. She had the same look the shrink had. What is going on? Just please come get me, I really need a fucking drink.
~Dean
Day 260: Sammy, It has been a while. Still nothing from you. Nothing has changed on my end. A couple of weeks ago they let me go outside. It was raining and reminded me of the times we would sit in the back of Baby listening to the rain, trying to fall asleep. Do you remember? When Dad would go on a hunt. I do. The whining is very loud today. I wonder what it means. I miss Cas and you, and mom, Dad, Bobby, Ben, Lisa, Jo, Ellen. I miss everyone. I can't stand it in here. I need a fucking drink. Please just come fucking get me.
~ Dean.
Day 300: Sammy, my poor brother, They finally told me today. What happened in the church. I remember now. I was too late. I failed you Sammy. You don't have to come get me. Sammy, what happened? Us Winchester's always make it out alive. What the fuck happened? I don't know why I am writing. It is hopeless. Please, if you can, help me, I really need a drink.
~ Dean
Day 302: It's over Sammy. We did some good in the world. Hell Is closed, forever. The apocalypse never happened. We truly did it. I will be with you shortly Sammy. I found a sharp piece of metal this morning and hid it under my bed. There will be no more need for letters. When I get there, let's go get that drink. ~Dean