[ Jack lets him go. He misses Castiel's hugs. They always made him feel better and he thought maybe he could give him that feeling of security too. But he just isn't good enough for that. He can't bring him comfort or fix his problems. He can only listen to him and show as much kindness as possible. Castiel might not want his love and unwavering support but he'll get it anyway. ]

I know you've made mistakes but that doesn't mean you can't change or you can't improve. There's always room to do things better next time. I learned that from you.

[ Perhaps Castiel only did that because he experienced so much hardship and let down and his own mistakes took over his life before. Existing through all of that made him stronger on the other side and able to be a different man for Jack. This was his difficult period of time when he struggled, and it's on the other end of it that he was different. It's Jack's duty to help him now. ]

Please, Castiel, you must sit. I can bring you the alcohol. You're going to start struggling to stand right. You should drink water too.

[ Jack's never been around someone drunk but he thinks he understands the basic idea. The full bar does have bottled water alone with soda and other options so they already have that down. ]