When Sam and Dean decide to settle down for good, Sam is able to get a pretty good job and hold it down and it gives him some stability, but Dean is unable to keep any of his jobs. He'll be unemployed and have nothing to do while Sam's at work, he just sits around feeling useless and driving around or drinking. Whenever he can finally land a job he's fired in a couple weeks. It's because of all his PTSD issues and alcoholism, he has trouble focusing and talking to people. Maybe has panic attacks at work and tries to hide them because he won't acknowledge that he's not okay. He's like, what's wrong with me??? Why can't I adjust like Sam can??? They realize he really needs to focus on getting better.
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