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.
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.
The article is not finished. Click on the next page to continue.
