personally, i think this is the moment where sam realized dean’s love for cas. i mean, sure, sam already knew dean loved cas ever since they started getting all buddy-buddy together. but this? this isnt just some love you feel towards your platonic best bud.
sam’s response is what got me. “i know you did,” he said, with a confused face yet a stern voice. he’s probably thinking–what are you doing dean? you told me yourself, you made it out alive. he didnt. we’ve had so many of our friends that died in the same circumstances, what made it any different? so he looks at dean’s face. really looks at it. and then he sees it. this isn’t a face grieving for his best friend. this is a face that says fuck i lost him i lost him and now im seeing him everywhere i couldve saved him and i didnt even get the chance to say i loved him holy shit i loved him what should i DO
Adding a little something to this, Dean’s “I just don’t understand why he didn’t try harder” is synonymous to “I loved him so much and I tried so hard to save him but he didn’t try at all? Because he didn’t love me enough to be with me?” And that’s one of the reasons why Dean made up the scenario where he doesn’t try hard enough to save Cas.
Let me make this worse about Sam’s awareness around that time. I don’t know who made the gif so I’m not going to post it, but during the infamous memed “boner alert” of cleaned up Cas, let’s not forget. Cas comes out, poses; Sam looks at Dean, smiling and gauging him; Dean, dumbstruck and possibly hiding a boner, gape-jawed upnods and glances at Sam glancing at him.
While I don’t really believe TPTB were necessarily going anywhere actively with it that season, I do often hold to the subtext behind Carver’s “3 year plan” and the amount of content, including by his own pen, that dropped to the cutting room floor after filming in S10. So I consider this an interesting AF territory.
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