Dear Castiel,
I hope this letter finds you well. I know that you are busy in heaven waging a war against your own kind to stop the reinstatement of the Armageddon, but I wanted to let you know I was thinking about you.
Not you specifically, of course. I am in no way pining over you in my lovely infernal pit. More accurately, I was thinking about you and Dean. Not that there actually is a you and Dean. We both know that Dean could not possibly be good enough for an angel of your status. With the most amazing set of black wings I've ever seen...
In any case, Dean has been nothing but dreadful to you. He is always whining "Me! Me! Me!" whilst you try so hard to just keep humanity alive. How can you stand it? If I were you, I would have flexed those amazing arms of yours and smote him long ago. In fact, I suggest you do that very thing right now.
It is no wonder you keep burning the eyes out of all my adoring followers instead of just asking me to remove them from your way. It's all the frustration of dealing with that buffoon and his moose brother.
But I forgive you, darling. I'll always forgive you.
Sincerely,
Crowley
Dear Castiel,
I have not heard back from you, but I am certain it is because of how busy you are in heaven. I would like very much to help you. Maybe we could come up with some sort of arrangement? I am a man of business, you see.
I have come a long way from my time as a crossroads demon because I respect the confines of a long term commitment. There are certain times I might bend the rules however. Like if a certain angelic friend is in need of me. We are friends dear Castiel, are we not?
An agreement that would benefit both of us would certainly help your plight. I propose to you: let me help you with construction of your machines of war, and in exchange, I only ask you to marry me. Or maybe some other binding commitment to serve me loyally for all eternity. It is strictly business, understand? I certainly don't want you to get the wrong impression of my intentions. While I bear the crutch of our matrimony, I will forever be married foremost to my work.
Then there is that oafish bullocks, Dean, who will agree to negotiate anything to with me under the pretenses that he should be allowed to threaten me with great calamity once the deed is done. There is no finesse to him. He's a buffoon . You see that, don't you Castiel? You need someone sophisticated and classy. Someone that looks smashing in a black suit.
On an entirely unrelated topic, how do you feel about beards?
Forever your friend,
Crowley
Dear Castiel,
Your angel messengers are morons. It has been over a week and still they have not delivered your letter to me. I don't want you to think for a moment that I have forgot about you. It would be rude of me to not respond to a friend who has taken the time to write me a letter. Don't you think it would be rude, Castiel?
I spoke with Dean the other day. He barely talked about you at all. He did mention you once though in an insignificant way and referred to you as "Cass". How insulting is he to think so casually of someone as powerful and angelic as you. You and I are far older and wiser than any human on this earth, but especially that human. He obviously doesn't care about you. At all. Why have you not smote him yet?
I have thought about the circumstances of your plight in heaven. Understand that me being your friend means that I worry about you and not just about myself. Don't expect the same graces from...others you might know.
I would like to discuss some ideas with you regarding our unifying for a common cause. Write to me please and let me know how to reach you more directly. A phone number perhaps?
Patiently waiting,
Crowley
Dear Castiel,
It was so good to see you on your visit to hell. You should have stayed longer. We could have talked extensively about our hopes and schemes while I made you a lovely cup of tea.
And may I just be so bold as to say that hell's inferno looks quite lovely reflected off your wings?
I know you were in a hurry. Insisting on knowing where Lucifer's cage was and all that lot, but you didn't need to be so forceful. Slamming me against the wall like you did has me seriously questioning your intentions. Have you not performed the same actions with a certain Winchester back when one might suspect you fancied him? Not that I think that now. Certainly not. However, comparing the two scenarios, I find them quite similar...
In any case, you botched your plans of rescue. If you had just asked me to help you, I could have assisted in removing Sam from hell's cage intact. Lucifer holds no ill will towards me. After all, you're the one he exploded.
All this could have been avoided if you had talked to me instead of taunting me with your aggressive flirtations. Nonetheless, I am willing to offer you a deal. As I have said before, I am a man of business and I feel that anyone's hearts desire can be obtained with the right amount of negotiation.
So I offer to free Sam's soul for you and return it to that empty hulking body of his, and in return, all you have to do is marry me. It really isn't that much of a sacrifice. Think of how wonderful it would be to have an angel and a demon, joined by eternal bonds, ruling hell for all time.
Not that Lucifer hasn't tried that bit, but you are a touch more appealing to the eye. And, you'll have me to help you. We would give heaven a run for its money then, wouldn't we, darling Castiel?
Consider my offer,
Crowley
Dear Castiel,
I think perhaps a letter is in order to clear up some things between us.
First and foremost, let me be very clear when I say I was not lingering at Dean's new domicile in an effort to see you.
It was simply coincidental that I happened to be in the area, doing highly important demon matters, when I just happened to notice you in flight. It was quite a sight by the way; to see you soaring across the sky on those brilliant wings like a burst of sunlight.
Nevertheless, I am sure we were bound to run into each other at some point in spite of your insurmountable schedule. You look brilliant by the way. The power of commanding an army of angelic wrath looks lovely on you.
What puzzles me is why you visited that Winchester human in the first place. You seemed to be staring at him raking his leaves. Were you perhaps looking for ways to take his life with the least amount of mess? I ponder that same thing often when I look at him. Humans are just so bloody.
It was nice so speaking to you there. When you spoke to me at last, and bestowed upon me your terms of endearment by calling me "Ass", I could hardly contain my racing heart.
Not that it means anything. You are simply a business partner.
On an unrelated matter, do you like destination weddings? Or something small and informal?
With all of hell's love,
Crowley
