I refuse to believe that back a decade ago that Dean looked at younger Lee and didn't at least have a crush. I've seen Christian Kane way back when, he's exactly who I imagine a closeted younger Dean would have hung out with and mentally done backflips around his attraction to him. He's just the right amount of cool and rugged to paint any feelings as just manly admiration.
Hi! I totally see where you’re coming from nonny and I thought similar til I saw the ep and I just saw nothing that led me to think this is what happened.
I know there’s a ton of people saying it’s now “canon” that Dean’s bi and they were totally a thing, but honestly I didn’t see this (and this is what I didn’t want to post about but a few friends convinced me not to let myself be silenced even though some of them even disagree because they’re good beans and want discussions rather than steamrolling in fandom).
Much of what I’ve seen as “meta proof” that Lee was acting romantically towards Dean was actually not scripted and imo Jensen’s usual chemistry and heart eyes at everyone acting or in one case of discussion I saw as heart eyes is Lee acting shifty because for example it’s when Dean brought up the fact that most hunters die and Lee isn’t giving him heart eyes, he is shifty because he chose to avoid that and to murder people instead, with a monster right below their feet. If you go into it from the pov that Lee is the bad guy and take away pre ep headcanons about him being Dean’s ex imo it’s far clearer to see his role in the story as the dark Dean mirror etc than anything else.
So, my headcanon (so not what canon has said because canon had no text about them being romantically involved, that’s all subtext and imo all that subtext was actually hinting at Lee being a bad guy, not being Dean’s romantic ex), so anyway my headcanon is that Lee IS totally Dean’s type, you’re right, so why is he not interested romantically?
Well, Lee as we know was a Bad Guy TM, and besides one night stands (and even then I can only think of the Amazon as a bad person when he was desperate for anything) Dean always chooses and is romantically involved with Good People. People who want to help others and basically a knight in shining armour. Lisa was to Dean, Cassie was focused on truth and exposing bad people, Cas is the ultimate Good Guy TM you know? As I discussed this with @wigglebox we love the fact that Dean not only IS the knight in shining armour but he drawn is drawn to them.
Now Lee is a Cas mirror opposite. That is clear, he even brings up their break up in the episode with the line about best friends leaving only if they had good reason to. He put himself before others and decided to kill people for his own gain, not even to live but just to have a better quality of life. He’s greedy and materialistic.
So my headcanon is that Dean always thought he liked Lee and John liked Lee, Lee is hot, but why is there a nagging feeling of doubt there that means he’s just not interested in him, weird! Then 20 years later he realises why he had that hesitation because he knows he’s a good judge of character and he should have trusted his instincts more.
Lee is a fantastic mirror opposite of Cas (and represents the ghost of John) as well as a dark mirror of what Dean could have been had he not chosen through his own free will to do the right thing. In fact I’m going to add wiggle’s tags here that he’s a nihilistic mirror of both Dean and Cas and actively apathetic, not wanting to fight and actively choosing the easy option which involves hurting others which is just so not them. He is many many things and I think he was fantastically written and acted by Christian. He is totally Dean’s type, so why didn’t Dean flirt with him when he’s on a break with Cas and why did Lee bring up Cas himself and why did we then get that scene with Dean and Cas?
Again I reiterate that this is my reading of the subtext as the text is vague and doesn’t point to anything in particular either way. I wrote more extensively about the canon text of Lee in another post but this is more my subtextual headcanon fun from your jumping point of Lee totally being Dean’s type :)
