9. Lisa and Ben
Lisa and Ben were the first opportunity Dean had at a normal life away from hunting. We first met the mother-son duo in season 3 when Dean checked in on Lisa, a fling he had a few years ago, to find out she had a son that seemed to be an exact replica of Dean’s personality. It turned out to not be his son, but when we saw Dean move in with the pair when Sam went to hell at the end of season 5 he sure did treat him like his own. Unfortunately, the pair no longer remember Dean, after having their memory of him wiped. Will Dean be able to reunite with them if they are able to close the doors to hell?
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