Supernatural wasn't short on storylines in the fifteen years that it aired. Dean certainly had his ups and downs in his life. Season 1 Dean, as a result, is a completely different person compared to finale Dean, who had seen far more terrible things than Season 1 Dean could have imagined and fought seemingly hopeless battles to save the world.
Finale Dean had sacrificed a lot, and had changed because of it. Losing people, becoming a demon, and all the times he died certainly affected him. Season 1 Dean would certainly approve, or disapprove, of certain aspects regarding finale Dean's personality and the things that had happened in his lifetime.
10 Hated: That He Became A Demon
Dean isn't a fan of demons, and for good reason. They're by no means good teammates, and they're known for double-crossing. Season 1 Dean would hate that he ever became one of the very things that he dedicated his life to hunting and eradicating from the world. Even worse, Dean tried to kill Sam while he was a demon, and that's certainly not a happy memory. Both Season 1 Dean and finale Dean hate this particular event, but luckily, Sam cured Dean before any more damage could be done, and Castiel stepped in to help.
9 Loved: That He Never Gave Up
Season 1 Dean didn't have much of a childhood and had seen plenty of terrible things in his 26 years. Yet, there was a lot more in store in the years to come. Between monsters, end-of-the-world scenarios, the losses of those closest to him, and mistakes made, Dean was understandably ready to throw in the towel a time or two in his life. However, he never gave up for good; he always prepared himself for another fight, even if he didn't think he had anything left to give. Season 1 Dean would've loved that no matter what, finale Dean hung in there and never gave up.
8 Hated: That He Lost So Many People Along The Way
Saving the world and fighting demons, ghosts, angels, and much more has its pros, but it certainly has its cons as well. Dean and Sam lost plenty of friends, and family, along the way. Losing Bobby was certainly heartbreaking, as was losing Charlie, Ellen, Jo, and Castiel.
Losing people was one of the worst downsides of hunting, especially when Sam and Dean didn't have many people consistently in their lives. Season 1 Dean would hate the fact that he lost so many people, especially since he'd already lost his mother at that point.
7 Loved: That He Got To Be With His Mother Again
The Darkness gave Mary back to Dean and Sam, allowing them the chance to be with their mother when they were robbed of her as they were growing up. It wasn't easy, as Mary had to adjust to the modern world and learn what her sons had been up since her death. Mary's relationship with her boys wasn't always smooth sailing, and they were separated when Mary became stuck in the alternate world at one point. Nevertheless, the fact that Dean and Sam got to know her again and spend time with her was a precious gift, and Season 1 Dean would've loved the reunion.
6 Hated: That He Never Settled Down
In the Season 1 episode, "Route 666", Dean is contacted by a former love named Cassie to investigate a series of deaths, including her father's. Though something still lingers between them, Dean leaves and doesn't see her again. The closest Dean ever comes to settling down is when he was with Lisa and her son Ben following Sam heading into the cage at the end of Season 5, with Dean believing he'd lost his brother forever. Dean decided to have Castiel erase Lisa's memories of him to keep her and Ben safe, but it wasn't easy for him to walk away from them, and he definitely regretted it. Season 1 Dean would hate that finale Dean never had a family of his own, but at least he had Sam.
5 Loved: That He Was The One To Kill Azazel
John raised Sam and Dean like soldiers, and while searching for Azazel, the demon behind Mary's death, he killed everything he could and saved people along the way. However, the Winchester family mission to kill the thing that had killed Mary lingered over them for years and had changed their family drastically, and still, it wasn't over, as Azazel eventually killed John too.
Dean was the one to shoot Azazel dead, finally getting the revenge he'd been trained his whole life to achieve. Though they had another problem to deal with, Dean could celebrate that at least Azazel's days of hurting his family were over, and that was something Season 1 Dean would've loved.
4 Hated: How He Died
Dean has died plenty of times, especially in the Season 3 episode "Mystery Spot." He's returned from both Hell and Purgatory. With all the gory and violent ways in which he's died, his final manner of death wasn't realistic for his character. Dean is a fighter through and through, and Season 1 Dean would've been incredibly disappointed that he ultimately died from being slammed into rebar while fighting vampires. He would've preferred something with more of a kick to go out with, as he always wanted to go out swinging.
3 Loved: That He And Sam Stuck Together And Saved The World Several Times
Season 1 Dean and Sam had a very different relationship compared to the one they forged over the years. They had been apart for some time, given Sam had left his family for Stanford, and obviously some tension still lingered because of it. Season 1 Dean had no idea that Sam would lose Jessica, or rejoin the hunting world, sticking by his side for years to come. Though he hated to see his brother lose her, Season 1 Dean would love that he and Sam became a team again and that he and Sam had the close relationship that they did in the end, and saved the world plenty of times while they were at it.
2 Hated: What Ultimately Happened To His Father
For the majority of Season 1, Dean and Sam were looking for their father; it was why Dean stopped at Stanford, as he needed Sam's help to track down John. Unfortunately, though, Dean and Sam ultimately lose their father to the same demon that killed their mother, as John makes a deal with Azazel to spare Dean's life in Season 2.
Dean felt guilty about it afterward and suffered for it; Season 1 Dean would've hated it just as much as finale Dean does.
1 Loved: That Sam Lived
Though it was incredibly hard for Sam to lose Dean one last time, he went on living and even had a son that he named after his older brother. Dean would be more than happy that Sam got a hint of that "apple pie life" after having so many years of suffering, tragedy, and heartbreak. Sam was strong enough to go on and live without his brother, and they eventually got a happy reunion in Heaven.
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