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Major spoilers ahead for Supernatural’s 300th Episode, "Lebanon".Supernatural aired its 300th episode which saw the return of John Winchester (Jeffrey Dean Morgan). There is no doubt that “Lebanon” was an emotional roller coaster, but there was something about the episode that felt incredibly familiar. But it wasn’t a lazy familiarity, it showed us just how much Dean has grown and changed in 300 episodes.
Dean has always had a desire to have a traditional, apple pie-style family. So when Dean is presented with a pearl that grants a person their heart’s greatest desire, Dean’s subconscious takes over and he’s granted the thing he really wants: his family. Namely, his father.
Of course, what starts as a touching family reunion soon turns sour as Sam and Dean realize bringing John into 2019 from the early 2000s has broken reality. Unless John is returned to his time, it won’t only return Mary to the grave, but it will also bring back Zachariah and the version of Castiel we met back in season four--the decidedly non warm and fuzzy version of the angel.
Ultimately, the choice is made to send John back to his time, and once again, Dean would have his happy family ripped away from him.
Of course, the episode felt familiar because Dean has come very close to having that family on a couple of notable occasions, only to have it stripped away from him. He formed a family with his girlfriend Lisa and her son, Ben. However, it soon became obvious that knowing Dean put Lisa and Ben in danger, and Dean decided it was better to erase their memory of him completely. He left their lives forever rather than risk endangering them.
In another episode, Dean was captured by a jinn and put into a dream of having a regular family. Though John is still dead, he died of natural causes in this scenario, rather than trading his soul for Dean’s life. And Mary and Sam are healthy and happy. Dean finally received the life he always wanted. However, when Sam rescued Dean in the real world, Dean had to choose between the peaceful, safe life he always wanted and his harsh reality. He picked reality.
In both instances, Dean was understandably crushed when he lost his family. Dean carries a lot of resentment towards his parents for not giving him and Sam a normal childhood, and because of his rough upbringing, Dean doesn’t really see his own worth. So when he's been separated from those he loves, it hasn't just broken his heart--it's told Dean wasn't deserving of a real family and happiness.
So, when he's losing Papa Winchester again in the 300th episode, it started to feel like the same old story. The thing is, this time, Dean didn’t react the same way to losing his dad. Dean handles it as well as anyone could and has a surprisingly grounded perspective. He explains to Sam how he’s let go of his anger towards both of their parents and that all he and Sam have been through has made them who they are--something that he’s finally happy with (or at the very least is comfortable with).
In this episode, Dean not only acts as though he can accept losing his dad again (however sad it might be), but he finds himself okay with where his life is now. It’s a huge revelation, especially since he was talking about hurling himself into the depths of the ocean for the rest of eternity with Michael, like, one episode ago.
It's growth for Dean--growth he may not even realize happened. He’s wrestled with his past and become healthier; it seems like he's actually satisfied, despite not having that apple pie life. Now if we can just get him to figure out how to ice Michael without tossing himself to a watery grave, we’d be golden.