That’s not even counting all the deals they made with demons just to save each other. Cas is trying to save the world.
What’s the tally for Diabolical & Winchester alliances?
Dean sold his soul to a Crossroads Demon
Sam tried to sell his own soul to a crossroads demon to release Dean.
Sam and Ruby were a twosome before and after
Sam agreed to be the vessel of Lucifer
Sam and Dean (and Bobby) worked with Crowley
I know I’m missing some. I’m trying to remember if they ever cooperated with Lilith.
Jesse (the Cambion kid) is still around somewhere. I wonder if he’ll be brought back into play. Since Castiel tried to kill him I doubt he’d allign with heaven but he might with Sam and Dean.
Back when she was still a Campbell, Mary made a deal with yellow eyes to bring John back in exchange for the right to drip blood in her kid’s mouth ~10 years later.
John made a deal with yellow eyes to take Dean’s place dying after the car accident.
As for Lilith, I just watched a rerun on my DVR last night where she tried to make a deal with Sam, she kills him and Dean, but then stops breaking seals. Sam pretended to play along, but before sealing the deal (with sex, a kiss wasn’t gonna cut it) he reached for the demon ganking knife. Then Chuck came in and she got outta dodge before the archangel came a callin.
Mmmm, man hugs all around!
Hell, he was probably just trying to be one of the gang - entry fee is making a deal with demons.
I really liked this episode - we all knew Castiel was doing wrong, but I had a feeling it was for the right reasons (as I said recently, they all but put a caption over his head saying, “The Road to Hell Is Paved With Good Intentions”). I liked the scene with Dean and Castiel having a heart-to-heart, and Castiel reminding us that he is still an angel, not a human - he has different powers, rules, and limitations. Plus, Misha Collins is awfully easy on the eyes. 
Castiel’s not the huggy type unfortunately (except in my fantasies, where he’s needy as hell).
And probably the closest they’ll ever get to sharing bodily fluids is choking up blood on each other.
I didn’t sense “holier than thou” so much as frustrating that Castiel waited all this time to admit his action, almost as if he was saving the admission for this particular occasion because he was backed into a corner and couldn’t avoid it. Both Sam and Dean know all about working with demons and unexpected consequences–after several incidents, maybe they’ve learned to confide in each other and have some kind of strategy. Maybe.
He should have stopped saying “It’s complicated” and “You don’t understand” and instead explained, “Here’s my exact situation. Here’s exactly what I’m doing about it. I will now answer your questions and listen to your advice.”
Then Sam could say something logical like “You know when a demon says that God chose you to be a leader by making deals with demons… God probably wouldn’t actually do that.” And Dean would figure out some way to run up to heaven and smack some people around. And THEN they could all hug.
But then the show’s problems would be solved quickly, there would be fewer misunderstandings leading to less angst and less reasons for Sam and Dean to look all pensive and thinking furiously . . . maybe this would lead them to solve problems like, which chippendales dancer stole the Axe hair gel, which pizza delivery guy was taking too long to deliver pizzas to the hot divorcee . . .okay what’s the problem?
Is the show on tonight?
No, it’s the Smallville finale. According to rumor, he finally becomes Superman. For real.
Two hours next week.
Wait, you didn’t see the episode last night? It was great! There was fighting, and ripped up clothing, and drunken snuggling, and in the morning Dean was making waffles dressed only in the trenchcoat. See, first Crowley disguised himself as Castiel and tried to sexually assault Dean, thinking that there wasn’t enough of a trust rift between them, and figuring that this didn’t technically run afoul of Cas’s order to not harm a hair on their heads or whatever, so of course Cas felt awful and shaken about that, and after all of them stomped Crowley into a bloody smear, Dean was like, “Look, man, it’s no big deal, you’re like a brother to me and brothers do this kind of stuff all the time.” Meanwhile Sam is like, “I don’t know what you’re even talking about, but I could really go for some waffles. I’m going to pop out for a box of Bisquik leaving you two all alone in this abandoned shack.”
Okay, maybe I totally dreamed that whole thing. And now I’m going out for some waffles.
Oh man, I can’t believe I missed it!!! Dude, it sounds so awesome.