Dean was, by nature, not very optimistic. This had served him well during his life of battling evil monsters; it prompted him to keep an extra knife under his pillow and gun in his belt, and had on many occasions saved the life of himself and others. On other occasions it caused awkward questions to be asked (example: when he attacked a friggin fairy and got arrested).
Sam often commented on his brother's inability to look on the bright side of things, and teased him endlessly the few times he pulled a gun on room service or a terrier he swore up and down sounded just like a hell hound.
Right now, Dean felt his pessimism was throughly justified.
Castiel still couldn't decide if he wanted to be sane or not. The angel currently sat slightly below Dean on a tree branch, alternating between swinging his legs (still covered in hospital patient scrubs) and frowning at the rattling twigs as though they had offended him.
It was quite possible that they did, though Dean did not want to contemplate that too deeply.
Oh, and let's not forget the most important thing!
He was trapped.
With every monster which had ever walked the earth.
Wait- He could see one speck of light in all this! Sam would be so proud knowing that some of his optimism had rubbed off on his brother.
Dean almost sighed, but kept his breath level instead. You never knew what was listening.
Yes he was trapped, but at least he had his new leather jacket.