Okay but how is Bobby Singer doing?
Bobby Singer, who was too afraid of becoming his father to have kids of his own. Bobby whose two boys grew up under his watch. He always wanted to believe that they would be happy, they would escape the life, but the negative part of him never quite believed it.
It was emotional enough for him to see Dean and Cas married. Knowing that Dean had accepted himself, was going to be with his soulmate made Bobby cry more than once at the wedding.
Little Sammy Winchester, who never fit into the hunter life, who always seemed to want to get out. Sam has grown since then, happy with hunting. Maybe he’ll never leave the life all the way, but Bobby knows if he didn’t it would be his own choice.
Bobby holds Sam close just before the wedding starts, gives him a bone crushing hug. He’s already crying, he can’t help it.
“Thanks for coming, Bobby,” Sam laughs, getting choked up himself.
Bobby pulls back long enough to look Sam in the eye. “I’m so proud of you, son.”
Bobby sits in the audience next to his grandson (Jack of course), who sits wiggling his feet around waiting for things to get underway. In all of this drama, all of this pain, Bobby’s boys have found happiness beyond anything he ever could have thought.
As he watches Sam see Eileen walk towards him, Dean and Cas nearby holding hands, Bobby realizes something: he has everything he’s ever wanted.
He has family. He’s somewhat retired. And most of all, he raised two boys and raised them well enough to see them alive, to see them happy.
That makes Bobby pretty damn happy, too.
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