Dean had Cas wipe Ben and Lisa's memories so they wouldn't remember him, and as horrible as that alone is, it gets worse the longer you think about it.
There were pictures of Dean in Lisa's house. He had a job at one point in her town. They had friends, people knew they were together. People knew them as Dean and Lisa, as a pair. He lived in her town, and people knew him from that.
So don't think about this fact occurring to Dean and Cas after they wipe Lisa and Ben's minds.
Don't think about Dean returning to their house to remove every trace of him that's there. Don't think about what he did with all those photographs. Don't think about him wiping videos from Lisa's phone, erasing his name from projects he did with Ben.
Don't think about Dean giving Cas a list of everyone he so much as had a conversation with in that town for Cas to wipe memories of him from. About how Cas combed the town for days asking people about Dean Winchester, and erasing the recognition from their faces.
Don't think about Cas hearing their stories and opinions about Dean before he does so.
Don't think about Dean walking through that town once the job is done and seeing people he knows. Don't think about him fighting the urge to wave, to say hi to people he once called acquaintances and friends. Don't think about the confused expressions on these people's faces when they see him, like they think he looks familiar but they don't know why.
Don't think about how far down Dean buried that life.
Don't think about the apple pie life Dean Winchester had and killed, the normal Dean Winchester, one that died long before the rest of him did.
The Winchesters have died many times, of course, but I wonder how many lives they've buried along the way.
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