5.18 "Point Of No Return" review

1. The less episodes left to go, the more intense and dramatic every one becomes.

2. Who exactly fired Zachariah, if God’s downshifted? Who are Zachariah’s bosses, anyway?

3. Drinking! Like Cas, like Zach.

4. I love this likening of Heaven to a business corporation. The destiny of the world could be a matter of round table negotiation! Very Greek comedy.

5. The meanest angels have always had one weakness – their devotion to serving their own career rise (cf. Ruby). Beware of workaholic angels. They can be dangerous for your health.

6. Must be really bitter to be laid off when you’ve put so much work and imagination into cajoling the two flannel-wearing guys who wouldn’t even have the finesse of taste to appreciate your découpages.

7. Zachariah doesn’t like people – it might be the reason why he sucks at human deals.

8. Dean taking a swig from a bottle must be one of the gayest things ever. Dean writing a letter is weird (honestly, do you even remember this man with a pen? It’s more of Sam’s weapon).

9. MIRRORS! in the opening scene. Dean is packing his precious leather jacket, car keys, the gun and the letter and picks up a second or two to glance at his dejected self in the mirror. Then he catches the reflection of Sam – the guy’s got ninja lockpicking skills – and turns around to face the actual Sam in the doorway. Cf. how it’s usually Castiel’s habit to appear behind Dan’s back in Dean’s mirrors and freak him out. Maybe it’s a subtle way to show how Sam’s going to act as a guardian angel of sorts for Dean in this episode?

10. Ha! Castiel doesn’t even ask for Dean’s permission and brings him where he should be. If Dean goes cunning on them, they are going to do the same to him. Castiel and Sam can quite co-work. The two probably have even more in common than Dean and Castiel – both are rebellious and disobedient. They have grown so much closer these days.

11. This hide-and-seek seems to be the reversal of the end of season 4, with Sam running away to team up with Ruby and Dean finding him.

12. Castiel’s been in despair in “Dark Side Of The Moon”, on a bender in “99 Problems”, but by now he’s worked his depression off. Dean, why don’t you follow his lead?

13. “You can’t give up, son” – “You’re not my father. And you ain’t in my shoes”. Mean, Dean, look at Mr. Singer’s face. You’re not in his wheelchair, either. And, sure, it wasn’t Bobby who saved you more than a couple of times and listened to you man-paining all this time. Sam’s expression is fantastically disapproving when he hears Dean’s words, too. Even Castiel, appropriately, gasps and flinches in pain – like it physically hurts the angel to listen to this rough insensitivity.

14. Sam’s quietly composed all this time, not hurling the “how can you do this to me” reproaches at Dean, just doing his thing. It’s very beautiful. 

15. Dean distances himself from them now (“You got nothing and you know it”). It’s a Him and Them situation. In season 4 Sam was in the same role.

16. Castiel sees a vision (like Sam’s visions, it also hurts) and flies off to look for what gives in some beautiful Canadian forest (I love these Canadian landscapes!) where he knifes to death a couple of Agent Smiths-looking angels (really, why are most angelic underlings in Supernatural dressed like the villains from “The Matrix”? To stress their robotic-ness?) – with not a twitch of muscle on his serene face – and then drags Adam by the hand out of the heap of dirty leaves (cf. “Lazarus Rising”. Adam’s grave is also marked with a ring of fallen trees) – not exactly raising him from perdition, but close enough.

17. Senior management must have sent this vision into Cas’ head – they’ve figured out how to use even him in their game against the guys.

18. It’s a very talk show episode, I like such ones especially.

19. Ha, Sam wouldn’t even let Dean take a beer from the fridge – or rather, Dean makes a big issue out of something even that small.

Dean: Move your remarkable ass, man, will you? I want to take a beer.

Sam: *thinks* Gimme your glass, I’ll pour your some.

Dean: Oh come on, it’s just a beer, not guns. What do you think, I’ll kill myself or you with it?

Sam: What if you crash the bottle on my head?

Dean: Why would I?.. *thinks* Good idea, though.

20. Castiel drags Adam to Bobby’s house on his back – so he does with Dean later in this episode. Funny how for once the angel has to do all the hard physical work.

21. In season 4, which body of Adam did they burn? I believe it was not the ghoul’s vessel, but the remains Dean had found in that abandoned tomb – so how is Adam coming back safe and sound and not zombie? And if he can return, after being burnt, so can their parents?

22. Adam’s story mirrors that of the guys. They were latchkey kids with a single father who was often away on hunts, Adam was a latchkey kid with a single mother who was often away on her nightshifts as a nurse. Obviously, Adam idolized his mother like Dean and, to a lesser extent, Sam worshipped their father, and he even picked up her profession – he was going to become a doctor, just like the guys became hunters after their Dad. The angels sweet-talked the naïve boy into being their bait, having promised him, among other things, a reunion with his Mum. The guys know perfectly well how easily family issues can be used against them, but Adam has yet to learn the sad truth – the hard way.

23. A sidenote: Dean’s nurse fetish might well be genetic – his Dad also loved women in white uniforms.

24. Adam has issues with John just like Sam did. Soul mates, you two? No wonder Sam and Adam click better than Dean and Adam.

25. I don’t know how they’re doing it, but the beautiful camerawork in the scene of the three pretty boys in one room talking and shooting glances at each other is megawatt slashy.

26. Supernatural trumps fanfiction! There’s so much potential in this scene.

Adam: *eying the panic room* I’d… I’d rather be going, thanks, guys, see ya.

Sam: Whoa, whoa, wait, wait. You ain’t going anywhere till we let you.

Adam: I don’t wanna stay here. It’s creepy.

Sam: No way, kiddo.

Adam: I’ll run away.

Dean: *advancing upon him* We’ll strap you down first. Pass me the handcuffs, Sammy.

It’s almost like “The Rapture” or something.

27. Sam does most of the talking and persuading. “Please, just trust me. Give me some time” – “Give me one good reason” – “Because we’re blood” – stop kidding me, my Mum’s my only family. The real!Adam sees his brothers for the first time ever, after all. Cf. Sam and Dean’s “You’re my (only) family” confessions at various points.

28. Sam, listening to Adam now, do you understand what hard job Dean has been taking all these years putting up patiently with your venting your family issues at him?

29. Adam’s Heaven – him with his prom date – is very Dean-like. Understandably, Dean perks up at this moment, asking the kid if he’d managed to actually screw the girl, but, characteristically, is cut short by the moralistic Sam.

30. Adam tells about the mission he’d accepted like it’s a game the Angels offered him to play, his boyish enthusiasm clearly shows he doesn’t get how serious matters with Michael and Lucifer are, and how silly he’s being.

31. Dean and Sam could have mocked the hopeful boy completely but they don’t like to hurt his feelings, no.

Dean: Look, Sammy, the kid wants to be a Michael… my ass.

Sam: The kid thinks he’ll waste the Devil with his bare hands. *laughs hysterically*

Dean: Angels told him! *doubles over with laughter*

Both: College boy thinks he’s so sma-ha-ha-art. *poke fingers at Adam*

Adam: Bitches.*hurts*

32. Seriously, Adam could have been the ultimate object of affectionate ridicule and brotherly pranking, so it’s good he never got to know Sam and Dean before he was old enough to talk back.

33. Sam’s suddenly in this authority position, he’s self-assured, knows what to do and has no doubts. And he’s suddenly between the Devil and the deep blue sea – he’s got not one but two brothers to watch out for and keep from escaping. Dean had pretty much the same task in “Jump the Shark”.

34. Angels may let go of Dean, after all – isn’t it one good reason to cheer Dean up? But no, it’s even worse for Dean. He’s so got used to the idea of Michael… By the way, if it wasn’t his brother the angels picked up as a substitute, would Dean bother to protest? No way I’m giving my Michael to you, milksob.

35. Sam’s supremely alert-eyed on Adam. “Going somewhere?” The very tone of his voice is gentle but firm, the “don’t even try to fool me” one. Adam could be answering “Yes, Sir”. “Tell you one thing, with an attitude like that, you would have fit right in around here” – Adam’s very conceited with Sam in this scene. And Sam probably feels like he’s talking to the younger version of himself, vociferous Dad rejector. Dean, take Adam along and you’ll be free from your fight championships at last: Sam and Adam would make perfect bitching companions.

36. When Dean makes flirty, familiar remarks to a man, that likely means this man has managed to win Dean’s trust. I guess the Dean-to-Cas flirt really started only in this season. “The last person who looked at me like that… I got laid”. Note that Dean does not specify the gender of this person.

37. Dean even winks seductively at Cas, and even Sam is amused with his brother’s wicked ways. But Castiel is looking at him with reproach in his eyes and then slams the panic room door shut in Dean’s face. Not so much because he’s learnt enough of humanology to have understood such a reference, but, arguably, because he doesn’t like the Dean of recent weeks, with his resigned attitude, and maybe he doesn’t approve of the bitterness he passes on Sam, too. Hilarious.

38. Dean and Sam’s heart-wrenching talk is the lowest point of Dean’s un-Deanness. Dean assumes Michael is strong enough to stand against Lucifer only in his body. Does he still believe in himself, after all? Dean won’t say “yes” but when he learns if he doesn’t then his brother will have to take it for him, he’s not about to let it happen. Gimme my cross back.

39. Dean says Sam is “angry”. Dean, and who asked you to tell him to “bury this crap” in one of the previous episodes instead of talking to him about his feelings? You get what you give.

40. While Dean’s mistrust of Sam in late season 4 was justified, the reheated burst of it now (from “99 Problems” onwards) was totally undeserved. Looks like Dean has never recovered from Sam having traded him for the monster, and now the bitterness kicks back. No gun left, so he uses the only weapon at his disposal and, Dean, you can kill with words, you know that? And still, I don’t really believe him here, don’t believe he believes his own words. It’s more like he’s trying to convince himself he doesn’t care about Sam – because otherwise he won’t be able to say his “yes”.

41. A Supernatural Soap scene:

Dean: Swinging both ways, Sam? First it’s Ruby, now it’s Lucifer. You’re totally quitting me, huh?

Sam: Look who’s talking. First it’s Anna, then it’s Castiel, now it’s Michael.

Dean: Demon lover.

Sam: Angel whore.

42. You nearly made him cry, you heartless bastard.

43. Even a year ago Sam would’ve raged, stormed off, punched Dean in the face – and quite rightfully – but he’s wonderfully meek now. He definitely realizes he can’t snap the last, fragile threads of peace and connection that bond them. Ironically, when Dean says Sam’s angry, Sam’s being far from it. His patience and forgiveness are endless. He even says “please” an awful lot in this episode. Cf. Dean’s evident choice to go with his brother even if he’s being evil (“I’ll even take Sam as is”) in “Lucifer Rising”.

44. “We can’t do it alone” is a tagline. Sam always needed this “togetherness”, even back in season 4, even when Dean didn’t appreciate the idea. 

45. Dean’s meanness goes as far as to send Castiel away to clear his way for escape. Nobody does that to an angel, man.

46. I get now how Future!Dean came about. This Dean is even worse, to a degree.

47. Adam falls asleep and Zachariah crashes into his ridiculously sentimental dream – or does he concoct it? Adam’s dream involves a park playground he used to go to with his Mum on weekends when he was a kid – cf. Dean’s fishing dream. God, I really want to see what Sam dreams about – why won’t Castiel or somebody sneak into the guy’s head?

48. Adam’s got second thoughts on the proposed deal, so what he bristled back when his brothers were trying to talk him out of it. Atta-poor-boy. 

49. “Psychotically, irrationally, erotically co-dependent on each other”. Couldn’t have put it more plainly. Though at the moment nothing shows it. Basically, Zachariah teaches Adam his twisted freaks of brothers are not to be trusted. But, unfortunately for Zachariah, looks like Adam did fall prey to the double awesomeness of Sam’s pleading eyes and Dean checking him out – the end scene is a proof.

50. Castiel’s the quickest draw! Dean did get his fair beating, only, surprisingly, not from Sam. This slashy Dean/Castiel fight breaks every rule of personal space. The men must have got perfect coordination to have kept their faces inches apart. And how much the fans’ waiting for slashy Dean and Cas action influenced the writing? Teasing, Supernatural.

51. Dean, no use opposing Cas, you know the angel has got body of steel, so don’t even bother hurting your knuckles. Castiel’s “I rebelled for this?” is the reverse of “Lucifer Rising”: back then Cas was in doubt till the very last moment, and Dean was in rage and ready to go. It’s completely changed now: Cas is the fervent one, Dean a slave to destiny. In 4.22 there was some minor Dean/Castiel fighting, too. And – hee – Dean now doesn’t resist, he knows it’s futile.

52. And no matter how hard Dean tried to bite Sam, Sam wouldn’t let their emotional issues result in a fight.      

Sam: *crying in the corner* Cas… why did he have to do it to me?

Castiel: Your brother is headed onto a dangerous road. You’ve got to stop him.

Sam: I can’t.

Castiel: Then I will. I’ll show this SOB better than to hurt his little brother.

Sam: Cas… promise me he’ll be okay.

Castiel: Don’t ask stupid questions, baby.

53. Amazing how in this episode everybody lays their cards open, without hiding their intentions for once and each of the men breaks rules of fair play, unashamedly using the tricks they’ve learnt from each other against each other. Castiel violently zaps Dean back home, Bobby warns the guys he’s contemplating suicide every morning, Dean uses the Angel Banishment sigil on Castiel and says Sam in the face how he thinks he’s “angry”, Castiel beats some rough sense into Dean’s brains, Sam locks Dean in the panic room.

54. Either of the three men had locked Dean down to the bed, and when he comes to, there’s just Sam by his side – and, look, after all the harshness Dean had put him through, Sam’s still not angry at him. Saint Sammy, indeed. It’s a very beautiful (not to mention homoerotic, what with the “wrist porn”) scene. In “Lucifer Rising”, Dean said he’d die for Sam but wouldn’t let him go evil, now Sam shows the same level of devotion. It must be a bit of a lesson for Dean. That he may go mad and hurl the most abominable insults at the guy, but nothing would shake his almost religious faith in you, you lucky bastard. Cf. Dean’s composure and determination in season 4 finale – only, his faith in Sam was probably not enough back then, and so Sam couldn’t make the right choice. Then again, Dean’s faith in his brother was put to harder tests, to be honest. Sam, after all, had never had to lose Dean to a “demon chick”, so it was arguably easier for him to keep this faith.

55. That Dean is ready to fight against Sam when (and if) he becomes Lucifer is scary, yet see how Dean’s being a big brother even in this – even if he’ll have to kill Sam, he’ll let no one else do it. John’s order, part two. The only consolation is, if he did have to do it, maybe he’d know how to make it as painless as possible. He doesn’t want this bleak duty snatched from his hands. He could always handle it his way but if it’s passed on to someone else, he wouldn’t be able to control what the vultures do to his evil brother – and then it’s better to accept the hateful mission rather than to give it away. That’s very Dean, and not quite as mean as it seems.

56. Sam’s “You can’t do this to me” in “99 Problems” – cf. “No, you won’t [say yes]. When push shoves, you’ll make the right call” here. The more determined Dean becomes to screw his life, the more faith Sam has. This “you won’t” and the scene around it is profound: Sam’s basically handing his life to his brother and lets him decide both their futures, he trusts him so much. And Sam knew if Dean did say ”yes”, he wouldn’t be able to fight it anymore either and wouldn’t have reasons to live and probably would say “yes” to the Devil. Sam was going all in. It’s already a highest form of sacrificiality in itself.

57. Sam’s being wiser – smart guy that he is, no matter if he thinks otherwise – if someone you love is hell-bent on doing something you think is stupid, there’s no stopping him – better let him get over with it already. Back in season 4 Dean denied Sam the right and ability to think and decide for himself, and it led to a tragedy: he thought of him as a little boy lost, which was, mind you, natural from the big brother perspective. But maybe because Sam is the younger one (and he even justifies the reason for his letting Dean have a free hand with Michael as Dean being his big brother) he’s inherently inclined to believe in his older sibling. He’s the only one who recognizes Dean as a fully responsible, grown-up man while neither Bobby nor Castiel think so at the moment (cf. again “Lucifer Rising” where only Dean was sure Sam wasn’t lost yet). Interestingly, both of them let Sam have his way with Dean – because maybe they recognize his knowledge of his brother is above theirs, anyway.

58. Dean has a huge crisis of brotherhood values in this episode, while Sam, on the contrary, is clinging to them, and it’s what saves them at the end. “The power of love” worked. They couldn’t handle that crisis back in season 4, but this time they both cope with it. It’s a test they’ve both put their trust to.

59. The setting, motives and the emotional drama in this almost pre-climax episode mirror these of “When The Levee Breaks” and “Lucifer Rising”. Only in reverse. Back then, Sam was going to do something Lilith stupid, now Dean is trying to do a “Michael stupid” thing. In season 4, Dean locked Sam in the panic room to stop him, now Sam does the same to him. Back in season 4, Sam begged Dean to trust and believe him but Dean wouldn’t, and that was part of the reason why Sam made his near-fatal mistake. Now, Dean is not asking for trust and just wants everyone to leave him alone. The difference is, Sam does trust him and believes in him, despite Dean being cruel towards him, and this faith proves crucial in Dean making the right decision at the end. Sam’s been there and done that, so he probably knows how important it is to have someone supporting you at hard times.

60. The way they keep encoding “because I love you” with “because you’re my brother” is amazing.

61. Castiel’s lost faith in Dean but he nevertheless goes out of his way to help them. This includes fighting five angels and carving the Angel Banishment Sign into his chest. It is clever that he uses his own body and hands to blow himself away with the enemies. Looks like a courageous suicide.

62. I bet he drops his scimitar to the floor especially for the boys to pick it up and fight Zachariah.

63. Castiel does nearly all of the physical fighting in this episode (angels, more angels, Dean), while the boys mostly fight their feelings, and, God, is that harder.

64. Now Dean’s found himself in a worst situation possible. Say yes or both your brothers will bleed to death. His dilemma is not simply say “yes” or not but betray Sam’s faith or not.

65. This “beautiful room” talk was a huge metaphor of the numerous scenes in previous episodes when somebody would put a gun in Dean’s hands and urge him to shoot his brother – but he would never comply.

66. They know it’s a trap yet still go there, because, frankly, they themselves must be tired of this Michael/Lucifer game and want it over with yet. Dean obviously knew Zachariah would pop up to do something nasty to Adam or Dean himself, or Sam to coerce “yes” from him, then was his intense confusion genuine or did he just play this desperate resignation up to fool Zachariah? If they knew they would be forced into such situation, why didn’t they strategize at all beforehand, going there with just Sam’s “no, you won’t”?

67. It takes one word – “Dean” – to help Dean make up his mind. Cf. that “When The Levee Breaks” scene where Dean, like Sam now, was lying on the floor helplessly and waiting for his brother to make his decision. Sam made the wrong one (who wouldn’t when you get called “a monster”), and Dean is making the right one – it feels like Sam gazing at Dean in pain, with hope, in disbelief, has done it. When he makes up his mind and winks at him, it’s like a burden has fallen from his shoulders, his face is lit with such doomed lightness.

68. Ha, Zachariah can hardly believe his luck.

69. By the way, it was real out-of-the-box-thinking. And could Dean have killed the angel unless he put up this condition first? It was clever, saying “yes”, getting what you want, and then backing out of the deal – cute, Dean, very Indiana Jones. 

70. Dean could take Zachariah throwing him in alternate universes, harassing and humiliating him, and even desecrating his mother’s physical image. But when Zachariah equaled their brotherly bond to an unhealthy erotic obsession, that was too much for Dean. Kidding!

71. Suppose he took Adam in his arms and led him out of the room – then they’d all be safe. Even if Sam remained locked there, Michael wouldn’t need him. And couldn’t Sam make it himself, without Dean’s helping hand? For Dean it’s an instinctive reaction to help Sam first and foremost, he probably didn’t have time or mental energy to figure out the right way, so no blaming him. Yet, ironically, Zachariah’s “they’d rather save each other’s sweet bacon” prophecy comes true – and that is bitter: hardly has Adam started to believe his brothers that they inadvertently leave him alone in trouble.

72. It’s not until Dean has dragged Sam a few feet away from this locked door (symbolism!) and onto the ground that he aims for the door again to Adam’s rescue. Maybe Dean’s “yes” got Adam trapped. And when he can’t open the door because it’s too hot he backs away a few steps and seems to be in a fix – like he considers if it’s worth entering now that Michael’s already there? Or maybe he’s just realized it’s too late?

73. Adam, after all, you wanted that. You get to be Michael’s sword and fight Lucifer. When Adam stops banging at the door and turns to look up at the blinding white light descending down on him, it’s not so much scare as it is confusion on his face. The kid sacrifices himself to save his elder brother, all the Winchester way, but without even wanting it – that’s the big difference between Sam and Dean’s sacrifices to each other.

74. Could Michael just have mistaken Adam for Dean in this mess?

Michael: *when it’s over* Oh. I think I’m in the wrong body.

86. Adam’s gonna be angry if he comes back. First the ghouls wasted the unfortunate boy, then his brothers put him into a trouble. Sam/Adam confrontations here might be like a rehearsal of “Swan Song”.

75. The boys seem strangely calm and even content on their drive back. The loss of both Cas and Adam seems to them both a less difficult problem than the huge personal victory they’ve just won together (and nobody but them can fully appreciate that). Look at the way Sam smiles when Dean says about not wanting to let him down and apologizes to him – like, told you so, like I was right. It’s a very beautiful smile, like he’s happy for himself and his brother, happy that his hopes, faith and trust were not in vain. Like he realizes what power he’s got over Dean.

76. Come to think of it, Dean did say “Yes”, only didn’t obey it.

77. Dean’s angoisse just slipped away from him, he’s back to give ‘em hell attitude at last.

78. This “I just didn’t want to let you down” confession is an understatement – in fact, he was staking the ground rules of his life on the line. And they booth know that. So much adorable code in here.

79. I don’t know how long it will last, but Dean acknowledges Sam’s not a kid anymore. Ha, the guy’s in his mid-20s, Dean, but being a big brother is for keeps, so we’ll see what comes out of it. “If you’re grown-up enough to find faith in me – the least I can do is return the favour”. Interesting how maturity here parallels faith and trust. Dean’s got used to the idea that he always knows better (“I’m older, that means I’m always right”), and when it turns out Sam knew better than him he grants him the ability to make decisions by himself. “We both know that that’s not you anymore” – to a certain regret, I guess.

80. But never stop being co-dependent, guys, please.

81. It’s season 5’s first climax, equivalent to “Lucifer Rising” in season 4, one more to go.

82. In early season 5 Dean’s openly declared mistrust (he had been on a low note and let that attitude come between them) led to Sam leaving him for a while but they re-united anyway, Dean had to apologize and admit: “Look, maybe we’re each other’s Achilles’ Heel, maybe they’ll find a way to use us against each other, I don’t know. I know we’re all we’ve got – more than that, we keep each other human”. Now, at the season’s end Dean again loses his faith and trust in Sam and does everything to make Sam leave him alone. He himself breaks up from him this time and almost loses his humanity on the way, indeed. But Sam knows better than that this time. When they re-join, the talk they’re having is creepily similar.

5.04 “The End”

Dean: Look, man, I’m sorry. (…) I was, uh – wrong. (…)

Sam: Thank you… I won’t let you down” (…)

Sam: So what do we do now?

Dean: We make our own future

Sam: Guess we have no choice.

5.18 “Point Of No Return”

Dean: I just didn’t want to let you down

Sam: You didn’t (…)

Dean: I owe you an apology. (…)

Dean: So screw destiny, right in the face. I say we take the fight to them, and do it our way.

Sam: Sounds good.

Both of these Dean’s apologies came at the outros of the episodes that featured a Dean-gone-inhuman. 

83. Also: in 5.04 everybody persuaded him to say “yes”, in 5.18 everybody wanted to keep him from doing this. Great.

84. Finally, the Supernatural Soap Summary of this episode:

Dean: *packing things* That’s it, Sammy, I’m going to start a family with Michael the Archangel.

Sam: What? Dean… and what about me? Don’t you love me anymore?

Dean: Dude, you’re my brother, for God’s sake. That’s just sick.

Adam: Hey, bitches, sorry to interrupt your sweet talk, but lemme tell you, Michael actually loves me.

Dean: What? Why? We’ve been JDating for, like, almost a year now.

Adam: Maybe it’s ‘cause I’m younger and all.

Dean: Man, that’s so insensitive. Look, I’m not saving you when Michael rejects your sweet ass. Don’t come crying on my shoulder. *man pains*

Sam: Come on, Dean, you know I’ll never leave and reject you, come on. *reaches out for him*

Castiel: *spying from the corner* Damn. Just when I thought Dean was mine. *rolls up sleeves*

85. Finally finally. Dean’s letter from the beginning of the episode (SupernaturalWiki has the text) is curious. And – yeah! – Dean can be quite eloquent.

(a) He’s not sure if Sam and Bobby receive his package at all. Does it mean he’s not sure if Michael-in-him wins?

 (b) Dean doesn’t think his decision is “giving up”. He compares his choice to what John did – it’s an inevitability, a necessary sacrifice prompted by the lack of other options and done to preserve whoever and whatever he leaves behind. That at least gives more insight into Dean’s reasons.

(c) Bobby is an “honorary Winchester”, according to Dean. I presume his family name is short of a nobility rank/knight order for Dean. 

(d) I love how he addresses Sam (just “Sam.”) and dedicated the last paragraph to him. He still remembers Sam once told him he prays (“Houses Of The Holy”?) every day, and, apostatic person that he is, asks the boy to pray for him. God, that hurts.

(e) “And Sammy, one Winchester lost to this fight is enough”. Dean subtly forbids his brother any thoughts or attempts to follow him in the dark. I may die but you live, I tell you. And look how at the end of the season it was Sam who turned out to be “the one Winchester lost to this fight”. And, really, it’s interesting: Dean doesn’t want Sam to say “yes” to Lucifer (so that he doesn’t have to fight him) and still hopes to off the Devil as Michael? How? Would Michael-as-Dean fight Lucifer in his Nick vessel? I guess, Dean wants to put some condition to Michael: we’re fighting the Devil but not the Devil as my brother. Dean wants to say “yes” – so that Sam doesn’t have to, be the first to do the damn thing.

(f) “When it’s over…”. When it’s over, is it a post-Apocalyptic no-man’s desert or Earth as usual? Looks like Dean hopes for the better.

(g) God, Dean, why couldn’t you explain all this orally so that your dearest and we didn’t have to think foul of you? Dean, you’re tragic and brave. We’ll pray.