Levi!Dean: He doesn’t have relationships. No, he has applications for sainthood.
‘YES. A thousand times yes. Dean has this tendency to view the people he loves as all good or all bad, and it’s probably one of his biggest faults inhibiting him from forming lasting relationships. By relating to people in this way, Dean condenses real, human individuals – who inevitably have flaws and weaknesses – into ideas, which can be clung to or discarded at will. In essence, he negates and erases their humanity.
But nobody can stand on a pedestal forever. We all make mistakes; we all fall eventually. And so Dean is bound to be disappointed by those he loves most, because he refuses to accept that everyone has flaws, even the people he’s closest to.
Dean does this, of course, because his own self-worth and identity are so damaged that he can’t conceive of himself in anything other than ideas: the Good Son; the Righteous Man; the Protective Older Brother; etc. He never learned how (thanks, John). And Dean hates himself so much for not being able to live up to these roles – imposed mostly by outside sources – that he compensates by erasing the weaknesses he sees in others, because by doing so he can justify his own self-loathing (as in, “these people are perfect, which only makes me look that much worse in comparison”, etc.). If they weren’t perfect, then they’d be like him, and in Dean’s mind, he loves these people too much to think so poorly of them.
(Where did Dean learn to relate to people this way? From his father, John Winchester, of course,who placed Mary on such a high pedestal after her death that the real thing was bound to hurt and disappoint her sons when they eventually met her. Nobody could live up to the St. Mary Winchester, not even Mary Winchester. But that’s another analysis for another time.)
Nowhere is Dean’s tendency toward erasure more apparent than with Lisa. Somehow Lisa went from being the “bendiest weekend of my life” to the idealized family that he never thought he could have (mostly because of his interactions with Ben in “The Kids Are Alright”, I think). Jensen himself has even confirmed that Dean wasn’t in love with Lisa so much as he was in love with what he thought she represented. And that’s why, I think, their relationship was doomed to fail: because people don’t represent family, or peace, or closure. They’re just people.
Season 6 does some brilliantly clever things with point-of-view to underline this point. Many people complained (myself included) that Lisa lost any semblance of personality she’d once had this season, but consider that for this arc, Dean is our POV character, not the generally omniscient POV we had for the previous five seasons. So what do we, as the audience, learn about Lisa through Dean’s eyes? Not much, other than that she is pretty, and comforting, and puts up with his crap. They have nothing in common. We see them do nothing together: no shared hobbies, barely even any conversations that don’t revolve around season plot points.
Indeed, we learn far more about Ben – we hear about his school projects, we see him help Dean restore a car. And when Dean arranges to die in “Appointment in Samarra”, the letter he writes is addressed to Ben, not Lisa, or Lisa and Ben.
Lisa remains a big question mark, which is not how she appeared in “The Kids Are Alright” – also written by Sera Gamble, by the way, which suggests to me that her character erasure here was entirely intentional. It’s a hint that Dean doesn’t really see Lisa as anything other than an idea, as the Saint That Stayed With Him. (Sound familiar? It should, as that’s what Meg says of Cas in “Reading is Fundamental”.)
Character-wise, Dean needed the Lisa and Ben arc; he needed this gigantic fuck-up in his life, because it shows him just how disastrous and harmful his tendency to idolize people can be. And it’s a big stepping stone as to why he tries so hard to reach out to forgive Cas in the end of Season 7. Contrary to popular criticism, Dean is growing. Dean is evolving. He’s learning what acting like a man really means.
But I’m getting ahead of myself here.’