Perhaps he's on a self - imposed exile. Dean has always been the type to take on burdens himself. He could have discovered something about himself, like a dark prophecy related to him endangering Sam or his friends, and decided to disappear to keep them safe.
There could be many reasons. Maybe he ran away from home because of some family problems. Or perhaps he was lured away by someone promising something exciting. Another possibility is that he had an accident and ended up somewhere unknown.
Well, there are several possibilities. She might have gotten lost, or someone could have intentionally taken her. Another option is that she wanted to start a new life on her own and disappeared intentionally.
It could be a mystery or a crime plot. Maybe he was kidnapped or went into hiding to escape something.
Maybe he got lost in some remote area. Or he could have been kidnapped and held captive by bad guys.
Maybe Dean gets cursed by a witch. The tail could be a side - effect of the curse that slowly changes him. He has to find a way to break the curse while still hunting monsters, and Sam has to deal with his brother's new 'accessory' and the problems it causes during their hunts.
Some fans speculate that it's a setup for a major character arc transformation. They think that his disappearance will lead to him coming back stronger and with new powers or knowledge. For instance, he might encounter some long - lost angels or a new type of hunter who will teach him unique skills.
Well, it might be due to lack of interest from the writers over time. As the fandom evolves, new characters or storylines might become more popular, causing writers to shift their focus away from Draco Malfoy fanfiction. Also, some fanfiction might disappear if the authors themselves decide to remove it for personal reasons, like they no longer want to be associated with that work or they have rewritten it into something else.
Sometimes it's due to Dean's overprotectiveness. He might think he's doing what's best for Sam but in the process, his actions end up causing harm. For instance, he could keep Sam from a mission that Sam believes is important, and in the struggle, Sam gets hurt.
One possible plotline could be that Negan initially tries to assert his dominance over Sam and Dean. He might see them as a threat to his own 'rule' in the world of the fanfiction. But Sam and Dean, being the hunters they are, would not take kindly to his posturing. They could end up in a battle of wits and strength. Another plotline could be that Negan has some information about a powerful supernatural entity that Sam and Dean are after. So they have to form an uneasy alliance. Sam might try to reason with Negan while Dean is more on the side of being cautious and ready to fight if needed.
One possible plotline could be that Dean is working at the truck stop to keep an eye on some supernatural activity in the area. Maybe strange disappearances of truckers are happening, and he's undercover to figure out if it's a demon or some other evil entity causing it.