Everything is Almost Fine

[COMPLETED]

"What- what about Cas?" Dean asked, he'd watched someone very close to him sacrifice himself to save the world. To save Dean. He couldn't handle the idea of the angel staying in the empty while he and Sam lived out the rest of their lives.
"Oh, don't worry," Jack said, a smile still on their face, "I'll see what I can do. I'm not letting my father rot in the empty for eternity."

~ Or ~

After Dean asks Jack to bring back Cas, he starts to think about his feelings.