Please note: the "But Nothing Really Ends, Does It?" section below contains possible spoilers, since it mentions the CW's general description of season six during my speculations on what might happen.
5.22 Swan Song: I Got Something To Say
Lucifer takes Sam;
Dean and the car bring him back.
Promises break hearts.
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Read the longest commentary in history... pour a drink first! )
Just as an aside, your commentary reflected on the role of Castiel. "I think Castiel used his new powers to bring Bobby back of his own volition...."
It occurs to me that Castiel's restoration of Bobby's good health was more than just out of respect for the hunter and consideration for Dean. I think Castiel was sincerely distressed he could not heal Bobby after the stabbing incident which confined Bobby to the wheelchair. With his angelic mojo returned, the "new and improved" Castiel seemed to derive as much satisfaction in Bobby's rejuvenation as did Bobby. As for healing Dean, Castiel was also honouring a promise to Sam he never thought he'd be able to keep.
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I like your take on Castiel's healing of Bobby. I think you have a definite point; Castiel hadn't been able to help before and now he could, and that helped to make up for earlier failings. And I think you're absolutely right; he derived satisfaction from being able to do it.
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