It's worse because you know that, for Dean, given what he expects to do with his life (and thinks that he should be doing), that's as good as it's ever going to get. It was so painful to watch him struggle through saying that, and to still be told "No" in the end. Jensen rocked my socks off with this episode's acting in his angsty scenes, and that one was the prizewinner.
These are stolen from comments I made in maygra's journal...
The biggest heartbreak of this episode was Dean finally saying what he's never said and has tried to avoid saying, and then... it didn't make a difference. Not from Dean's perspective. He knows Sam loves him, but Sam won't stay-- and given that he's a key component of what passes for happiness in Dean... *Sigh*. Just made me think, this is how we teach people not to reveal their feelings-- we pass over them or punish them if we do.
And yet, I totally understand Sam's not wanting that. I feel worse that this is all Dean aspires to, actually.
At the end, I may have gotten something different from that last scene than most people. I saw Sam feeling what Dean had felt before-- having to let someone go that you'd finally gotten back, when every part of you was screaming to hang onto them. And I saw Dean realizing that Sam feels that now, and maybe understands... but it still didn't make Dean feel any better (he was the most teary-eyed of anybody in that last scene with their dad, it seemed).
Hmmm. *Unpopular opinion warning* I am again not feeling the Papa Winchester love. I get that he loves his boys, and I truly believe he does-- and that he's doing what he thinks is right. But at the same time, that militaristic interaction they have with him really rubs the wrong way, and the fact that Dean can't fathom normalcy-- will never have his own children and family for instance... I know their father didn't do that to them on purpose, but it still reflects very badly on him in my book. He's a gray character (like a real person)-- he's not going to go much closer to the white for me, that's for sure. *Sorry*
I still hate the Meg actress, but I do like the Daddy Winchester actor (more than his character).
Interesting noire overtones to this episode (it was mostly endless night throughout), and it amused me no end that it was set in Chicago but yet... who could tell? :0 Granted, I haven't been ALL over Chicago, but this looked like any bar and any warehouse district of any large city. Where's the creepiness down by the lake? The Els? The River? Budget. What was that? Budget. Damnit, can't you pull your asses out of Vancouver at least once a season?
Loved the daevas, though.