Building a family with Lisa and Ben was one of the . He was finally given a regular life, and he had genuine connections in the wake of Sam's imprisonment. He really built something good for himself.
Dean is a beloved character with a horrifically tragic past.
It's no wonder that fans love a relationship that saw him actually get to break away from his life as a hunter. Dean had the chance to be normal and, given how hunting ended for him, there was no better relationship than one that got him out of it.
The very opposite of Dean's relationship with Lisa, Benny was a character who drew out the hunter in Dean. As a vampire who fought alongside the hunter in Purgatory, Benny had already seen the worst of Dean by the time they returned to Earth.
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