10 Dean Hunted Even After He Started A “Normal Life”

After Sam went to hell at the end of season 5, Dean returned to his old fling, Lisa, and her son, Ben, and attempted to have a regular life, bidding farewell to hunting. He even retired his beloved Impala during that time. Despite his grief and paranoia from a life of monster-hunting, Dean was relatively happy having a family.

However, shortly after Sam showed up, Dean slowly slipped back into hunting. Ultimately, this led to one of his fears, namely Lisa and Ben in danger. Crowley's demons kidnapped them, one of whom possessed Lisa and stabbed her, nearly fatally. Without Castiel, she would've died, arguably because Dean didn't steer clear of the hunting life as he had intended.

9 Sam Trusted Ruby The Demon

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One of Sam's most problematic decisions was trusting Ruby, even after discovering she was a demon. Unlike some other choices, Sam's decision to follow Ruby's lead was continuous, despite admitting his reservations about her. Additionally, , but instead, their volatile relationship slowly led to Sam's demon blood addiction.

This was something he was conflicted about and ashamed of since it was one of the many things he kept from Dean.

To make matters worse, Sam stopped Dean from killing Ruby in season 4, episode 21. Had Dean killed her then, Sam would not have freed Lilith, necessarily, which would have prevented Lucifer from escaping hell. If the seals had been left as is, the destruction and chaos Lucifer caused once he was topside wouldn't have happened.

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