do you think, had jess not have died and sam did get his happy ending with her, dean would be envious of the life, in a way? would he be silent about it and go on about hunting or would he consider having someone of his own, and maybe trying to start a family too?
if we’re going with the mindset of 26-year old dean, then yes, he would be envious and he would continue hunting regardless. in his mind, sam abandoned his family for a normal life which is something dean can never see himself doing. that being said, if john died, dean would probably consider settling for a normal life, too, because it’s what he’s always wanted for himself. but, as long as his father is alive, he cannot leave him behind the way sam did.