PREVIOUS CANON POINT: S4, E22 NEW CANON POINT: post S5, E22, in some random timeframe between s5 and s6. He'll have memories of his life with Lisa & Ben, but before the start of s6, when Sam comes back.
CHANGES: There aren't too many changes personality wise, but there is a time jump here of about...a year, ish. Dean is still codependent, still reckless and self-sacrificing, but the most notable thing here is that for the first time, he listens to his brother, and acknowledges that Sam is a grown man, capable of making his own decisions. Dean has been looking out for Sam his entire life, essentially raising him, and it's a hard thing to let go of when you've had that kind of mindset for thirty odd years.
It's a sign of maturity that Dean actually lets go and allows Sam take the wheel. Sam makes his choice, and Dean backs his play - and ultimately watches as his brother jumps into Lucifer's cage, Lucifer and Michael in tow. Dean is devastated by grief, out of his mind with it, and it shows. He turns more towards alcohol and is obsessed with finding a way to bring his brother back, despite his promise to Sam not to look. The only promise he does follow through with? To go to Lisa (you know, that chick Dean had a one night stand with and has seen like, once since? thanks Sam), and start a life with her and Ben (and frankly I am a firm believer ben is actually deans, idgaf what kripke says).
He will be more morose, more fixated on alcohol as a coping mechanism, incredibly depressed, and consumed with guilt over what happened to Sam, what happened to the Harvelles (he believes this is his fault), and honestly - he quietly, very, very secretly, regrets not being able to get to Michael to say 'yes' to being his vessel. If he'd gotten there first and managed to fight Lucifer in Nick's vessel, then...well. Maybe paradise on earth isn't so bad.
He will be absolutely willing to throw himself into missions more in order to fix his regret - because if he can fix that, then the Apocalypse never starts, and Sammy doesn't have to spend a friggin' eternity in Hell, tortured by Michael and Lucifer.
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PREVIOUS CANON POINT: S4, E22
NEW CANON POINT: post S5, E22, in some random timeframe between s5 and s6. He'll have memories of his life with Lisa & Ben, but before the start of s6, when Sam comes back.
CHANGES: There aren't too many changes personality wise, but there is a time jump here of about...a year, ish. Dean is still codependent, still reckless and self-sacrificing, but the most notable thing here is that for the first time, he listens to his brother, and acknowledges that Sam is a grown man, capable of making his own decisions. Dean has been looking out for Sam his entire life, essentially raising him, and it's a hard thing to let go of when you've had that kind of mindset for thirty odd years.
It's a sign of maturity that Dean actually lets go and allows Sam take the wheel. Sam makes his choice, and Dean backs his play - and ultimately watches as his brother jumps into Lucifer's cage, Lucifer and Michael in tow. Dean is devastated by grief, out of his mind with it, and it shows. He turns more towards alcohol and is obsessed with finding a way to bring his brother back, despite his promise to Sam not to look. The only promise he does follow through with? To go to Lisa (you know, that chick Dean had a one night stand with and has seen like, once since? thanks Sam), and start a life with her and Ben (and frankly I am a firm believer ben is actually deans, idgaf what kripke says).
He will be more morose, more fixated on alcohol as a coping mechanism, incredibly depressed, and consumed with guilt over what happened to Sam, what happened to the Harvelles (he believes this is his fault), and honestly - he quietly, very, very secretly, regrets not being able to get to Michael to say 'yes' to being his vessel. If he'd gotten there first and managed to fight Lucifer in Nick's vessel, then...well. Maybe paradise on earth isn't so bad.
He will be absolutely willing to throw himself into missions more in order to fix his regret - because if he can fix that, then the Apocalypse never starts, and Sammy doesn't have to spend a friggin' eternity in Hell, tortured by Michael and Lucifer.