If you look at Sam and Dean wearing your codependency goggles, it’s not difficult to see a motherly dynamic in some scenes, when Dean fusses over Sam. This was most evident near the end of Season Eight, thanks to Sam’s trial sickness, but it can be traced back to early seasons too.
It’s not exactly difficult to see why Dean might get mother-hennish toward Sam. Dean clearly idolised their own mother- judging by Dark Side Of The Moon and What Is And What Should Never Be- and having only her and his father’s (and perhaps Bobby’s) examples to follow, growing up cut off from other hunters as they did, it’s not surprising that Dean would have become a weird amalgamation of his father’s and his mother’s behaviour.
Although out of the brothers it’s Sam who Dean is constantly poking fun at- about the food he eats, about his hair, his masculinity- it’s Dean who, macho as he undeniably is, also fulfils stereotypically feminine roles. When the boys move into the Bunker in Season Eight, it’s Dean who bustles around making burgers and cleaning.
And it’s pretty clear that Sam needs this sort of looking-after; Trial sickness quite aside, when Dean’s gone at the beginning of Season Ten, he looks like absolute shit. Even when Sam left Dean to go to Stanford, he had Jess- who bore some startling similarities to Dean. Then of course there’s the memorable events of Playthings. Face-grabbing, anyone?
Perhaps this is why many of the women they meet take on motherly attitudes towards Dean in particular- because they recognise that Sam already has a mother figure in Dean, but that there is no-one to mother Dean in turn. Ellen, Missouri, Lisa… the exception here would be Jody, who clearly has the stronger bond with Sam- even telling him ‘don’t make me use my mom voice’ in Time After Time After Time.
However, Time After Time After Time was one of the few episodes where Sam and Dean were parted, and Sam was one mother figure short- hence, Jody. Meanwhile, over in 1944, Dean had acquired himself a Bobby-esque mother figure of his own.
It’s clear that other characters agree that Sam and Dean really need someone to look after them, but the reasons are different for each brother. Sam is often a very open character- sometimes you just want to tell him to put his frickin’ heart away before a ghoul comes along and eats it or something- I mean, he’s 6″4 and when he cries he looks about nine years old.
Dean, on the other hand, tries so hard to be the tough guy, and he is, they both are- but sometimes something cracks his defences and he gets this lost little boy look. It very rarely happens, and notably, one of these occasions is around their mother. It’s as if Dean’s emotional side stopped developing after she died, and sometimes he just reverts back to being four years old and just having seen his mother burn up on the ceiling.
Guys. You’re so damaged. Go talk to Jody or something. Better yet, talk to each other! Everyone loves some codependent brother feels.