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These are the 8 phases of Chris's life so far. At what point was Chris unsalvageable and fucked beyond repair? I could see people making arguments for each one. Some people would say he was fucked at birth but I think Chris as a baby and child could have become fairly normal with proper parenting. Teenager Chris already developed a lot of his bad habits and would have been harder to fix but could have likely been taught to develop a work ethic and work simple jobs. By the time he became a manchild it was highly unlikely but there would have still been a tiny 0.01% chance sliver of hope if he was thrown straight into the fire and forced to adapt as a functioning human or at the very least learn how to budget his tugboat to remain in the status quo as a loveable idiot.
For these reasons I feel like the tomgirl era is when Chris could no longer be fixed. Most of us just figured Chris would remain the striped shirt manchild he always was and live on with his tugboat as a leach on society. It wasn't an ideal life but he could have probably made it work. Once he started shoving tampons up his ass and cutting open his taint with a knife it sadly became clear that Chris would end up being a abhorrent freakshow that dies in his mid to late 50s. After this point he became more and more delusional (or true to himself if you believe Chris would have fucked his mom regardless of trooning out) and it started a snowball effect that eventually led Chris to where he is now.