“You know, the Empty said that it wouldn't come for me until I had finally given myself permission to be happy, but with everything we have going on, with -- with Michael still out there, I don't see that happening anytime soon.”
Basically Cas’s True Happiness would be gained from insuring that the world is safe from supernatural threats and its problems are solved , as well as Cas’s mistakes being fixed . Cas would probably also have to learn to love himself and move past his feelings of guilt - Deans ~confession~ wouldn’t do shit because that’s not what’s keeping Cas from happiness - and even if Cas’s happiness was completely tied to a relationship , out of anyone it would be Jack , his son . But again , Cas’s character and closure isn’t tied to just a single character - he has more depth than that .
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