Lost Ending I think I Finally Figured It Out

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Even after all these years and the fact I love the show, Lost's ending still makes me cry yet so angry at the same damn time. I still can't figure one thing out though that is driving me banana's. That being the group's members Sawyer, Kate, Miles, Frank, Claire, Ben and Hurley. It Doesn't seem to be clear on what happened with them. My only guess is that whatever happened to bring these characters into the limbo, took place years, maybe even decades after the finale days on the island when Jack completed his duty as Island protector. I believe this because, when Jack didn't return, Ben says Desmond will live. Suggesting that Hurley help Desmond get off the Island. Also, Hurley asks Ben to help him, be the protector the Island needs. In limbo, Penny is with Desmond, in the church. I don't believe she ever stepped foot on the Island, especially the last time the group was there. Ben and Hurley's flash backs ended of the Island ended when Hurley asked him for his help. Outside the church, Hurley says to Ben you made a great second. In which Ben answers by saying he made a great first. This indicates that Hurley and Ben spent a long time together on the Island after the last days. It's hard to say how long.... looking at how long Jacob was Protector, with Richard at his side. For Sawyer, Kate, Claire, Miles and Frank the Island flashbacks stopped abruptly when Frank stops the plane stating they have late arrivals. We get one last Island flashback once Jack finally realizes the truth. This flashback is of him seeing the plane successfully leave the Island. The five on the plane with Richard, obviously returned to their actual lives before ending up living in limbo with the others from the Island. This is why, they had an easier time letting go. While Jack and Locke fought it for a longer time and were the last two to figure it out.