One of the things I keep hearing about the Lost finale is that the Sideways was rendered meaningless by the revelation of what it actually was.
I think that's actually the OPPOSITE of what was true. The Sideways, which was actually an Epilogue, showed everyone the type of life they could have led. It wasn't arbitrary, though!
Christian says at the end that they collectively created this space. If that's true, then everyone CHOSE (if subconsciously) to make the changes in their lives. But in fact, everyone gave up something to gain what they did.
Jack's biggest fear was becoming his father, and he did. But he got a chance to fix it, to BECOME the dad his never could because he was too busy dying.
Sawyer got to be a good guy, to leave behind the conman, but in return his parents still had to die to set him on that path.
Kate got to save her stepfather, to make her mom happy, but in return she had to stay a fugitive instead of going to the island and later getting freed.
Sayid got to keep Nadia alive and (relatively) happy, but in return he could never have her.
Jin and Sun got to have a much more stable relationship without Jin turning into the cold asshole that he became, but in return they had to hide their love and risk everything to get away.
Ben got to not be a psychotic mastermind and actually be a cool guy, but in return he never got to have the daughter he loved (and even worse, had to watch her from afar).
Locke got to have a father and a wife, but he was still in a wheelchair and more importantly never got to discover the island and thus the faith that gave him purpose.
Hurley got to use his wealth without extraordinarily bad luck, and uh...well he was kind of awesome but no one loved him I guess.
Charlie got to keep being a damn rock star, but he still had that nasty heroin habit.
And so on.
Okay, so if we assume that the Losties somehow enacted these changes based on what they wanted for themselves or for others then the Sideways was them basically trying to fix everything they thought was wrong with their lives, even if it dropped them in worse situations first.
It's not irrelevant, though. In fact, it's in line with, more than anything, the first season. In the first season we got everyone's backstory, and it was always related to something that was going on on-island. They all had mistakes, regrets, things they wanted to fix, and on the island they often got a chance to do it. But regrets don't just go away, they stick with you.
So everyone carries these regrets into death, especially the 90% of the cast that died prematurely. In their shared afterlife, they all try to fix these things in some ways, either before or after the flight. But the truth is they have to abandon the things they want to change and remember the things that made their lives matter more than the changes they made: the connections with other people, specifically the other castaways.
As Rose says in the first Sideways, "You can let go now." She says it to Jack, who is the last to let go of his life because he doesn't want to believe that what he has isn't real. But subconsciously, I think he knows that he's dead and he doesn't want to stop trying to fix his life.
Ben chooses not to go with everyone, possibly because he has the largest gap between the life he led and the ideal one he gave himself. He doesn't think he deserves it, and maybe he doesn't. This show was about the choices we make and the chance to start over, but the truth is you can only start over so many times.
The island gave everyone a second chance, but you can't keep trying forever. Eventually you have to let go, to boil life down to the things that made you happy and move on.
And really, Rose is telling us to let go too. We all have things we would have changed about Lost, a way we wish it would have gone or something it would have done. But it has to end, and we can't control the ending but rather have to accept it and remember the moments that made us love Lost in the first place, because those moments will stick with us infinitely longer than how it ended or the missteps it may have taken. In the long run, no matter how much people say the show needed to be about mysteries and answers, they will always remember Sawyer and Juliet reuniting in death more than that dumb ol' bird that might have said Hurley's name.
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