Dean disappeared with the Mark of Cain. Sam tried his best to find him, though Demon Dean didn't want to be found. Castiel was with Hanna, another angel.
Castiel was the one to cure Dean of his demon-ness, while running on stolen grace. He got his original grace back, however, though not at full power.
Castiel helped to find Claire a new home. Sam found a book that could help cure Dean, but had to deal with Rowena. Inadvertantly, Charlie was killed.
"I think it should have been you up there," Dean said before going on his Stien killing rampage.
That stuck with Sam. Regardless, he and Castiel tried to find Dean, spending time together in the process.
The brothers were left with a cloud of darkness beginning to cover them, and Castiel was about to kill Crowley.
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Sastiel Through the Seasons
FanfictionCastiel had been observing Sam for years, even before the angels came to Earth. Seeing the boy was one thing, meeting him was another.