I think I figured it out
Part of what was bothering me about Dean's speech at the end of 6.16, anyway. I was watching season one's "Salvation," and there's a similar moment, from Sam:
Sam: Dean, uh.... I want to thank you.
Dean (looks confused): For what?
Sam: For everything. You’ve always had my back, you know? Even when I couldn’t count on anyone, I could always count on you. And now... I don’t know. I just wanted to let you know. Just in case.
Dean: Whoa, whoa, whoa. Are you kidding me?
Sam: What?
Dean: Don’t say just in case something happens to you. I don’t want to hear that freakin’ speech, man. Nobody’s dying tonight. Not us, not that family, nobody... Except that demon. That evil son of a bitch isn’t getting any older than tonight, you understand me?
Sam nods and Dean turns back to the house.
Compare this to Dean's speech from 6.16
Bobby: It was Omaha, it was my fault. And he never let it go.
Dean: Well, he should have.
Bobby: You don't know what I did, Dean.
Dean: Doesn't matter.
Bobby: What do you mean, it doesn't--
Dean: I mean at the end of the day, you two were family. Life's short. Ours are shorter than most. We gonna spend it wringing our hands? Something's gonna get us, eventually. And when my guts get ripped out, just so you two know? We're good. Blanket apology, for all the crap that anybody's done, all the way around."
Sam: Some of us pulled a lot of crap, Dean.
Dean: Well, clean slate.
Sam: Okay.
There are obvious differences in context, of course; but on the other hand, I think it's more complicated than I thought at first glance. After everything that's happened in this season around Dean and having a family, a life outside of hunting, I'm no longer sure that speech was as positive as I first thought. Not when you compare it to Salvation. There's a fundamental shift there, and I'm not sure it's one for the best. AND ADDING as I just picked up on it in a comment: Not to mention the specificity of Dean's wording about his death, in this particular speech: his guts ripped out? You mean, like before you went to hell, Dean?
I DON'T KNOW, GUYS. Maybe I am reading too much into this. But Dean's talking about the inevitability of his death, all of their deaths, due to their lives as hunters. I can't really see this as a good sign, even if it's a realistic evaluation of circumstances, and his suggestion of a clean slate is on the balance a good idea. I have thoughts on that too, and why I think blanket apologies/forgiveness might not in the end really work, but this stuff is complicated! I dunno. I think his impulse here is somewhat of a positive step for him, even if he's framing it as "we're all gonna die."
We're back to this, from season 4's "Criss Angel is a Douchebag":
DEAN Man...hope I die before I get old. Whole thing seems brutal, don't it?
SAM You think we will?
DEAN What?
SAM Die before we get old.
DEAN Haven't we both already?
SAM You know what I mean, Dean. I mean, do you think we'll still be chasing demons when we're 60?
DEAN No, I think we'll be dead...for good. What? You want to end up like -- Like travis? Huh?Or Gordon, maybe?
SAM There's Bobby.
DEAN Oh, yeah, there's a poster child for growing old gracefully.
SAM Maybe we'll be different, Dean.
DEAN What kind of Kool-Aid you drinking, man? Sammy, it ends bloody or sad. That's just the life.
And finally, I think it's probably appropriate to close with Rufus's speech from season 3's "Time is On My Side," the last episode before Dean actually does die, and our introduction to Rufus himself:
RUFUS
Kid, can I ask you something?
DEAN
Sure.
RUFUS
You got 3 weeks left. Why you wasting your time chasing after that skinny, stuck-up English girl?
DEAN laughs, but with a measure of discomfort.
DEAN
How’d you know about that?
RUFUS
Because I know things. I know a lot of things about a lot of people.
DEAN
Is that so?
RUFUS
I know aint no pea-shooter gonna save you.
DEAN
What makes you so sure?
RUFUS
Coz that’s the job kid. Even if you managed to scrape out of this one, there’s just gonna be something else down the road. Folks like us, there aint no happy endin’. We all got it comin’.
DEAN
Well, aint you a bucket of sunshine?
RUFUS
I’m what you’ve got to look forward to if you survive. Which you won’t.
I take it back, I have one more piece to close with, from the opener to this current season:
Dean: How long?!
Bobby: All year.
Dean: Oh, you got to be kidding me.
Bobby: And I'd do it again.
Dean: Why?!
Bobby: Because you got out, Dean! You walked away from the life. And I was so damn grateful, you got no idea.
Dean: Do you have any clue what walking away meant for me?
Bobby: Yeah -- a woman and a kid and not getting your guts ripped out at age 30. That's what it meant.
Dean: That woman and that kid -- I went to them because you asked me to.
Bobby: Good.
Dean: Good for who? I showed up on their doorstep half out of my head with grief. God knows why they even let me in. I drank too much. I had nightmares. I looked everywhere. I collected hundreds of books, trying to find anything
to bust you out.
Sam: You promised you'd leave it alone.
Dean: Of course I didn't leave it alone! Sue me! A damn year? You couldn't put me out of my misery?
Bobby: Look, I get it wasn't easy. But that's life! And it's as close to happiness as I've ever seen a hunter get. It ain't like I wanted to lie to you, son. But you were out, Dean.
Dean: Do I look out to you?
eta 2.0: I don't think this is as clear as I'd like it to be, but I'm still struggling to articulate for myself what I'm even trying to get at. I haven't written much (any) meta for this season and it's all kind of jumbled in my head, but I feel like at some point it'll come together!
Sam: Dean, uh.... I want to thank you.
Dean (looks confused): For what?
Sam: For everything. You’ve always had my back, you know? Even when I couldn’t count on anyone, I could always count on you. And now... I don’t know. I just wanted to let you know. Just in case.
Dean: Whoa, whoa, whoa. Are you kidding me?
Sam: What?
Dean: Don’t say just in case something happens to you. I don’t want to hear that freakin’ speech, man. Nobody’s dying tonight. Not us, not that family, nobody... Except that demon. That evil son of a bitch isn’t getting any older than tonight, you understand me?
Sam nods and Dean turns back to the house.
Compare this to Dean's speech from 6.16
Bobby: It was Omaha, it was my fault. And he never let it go.
Dean: Well, he should have.
Bobby: You don't know what I did, Dean.
Dean: Doesn't matter.
Bobby: What do you mean, it doesn't--
Dean: I mean at the end of the day, you two were family. Life's short. Ours are shorter than most. We gonna spend it wringing our hands? Something's gonna get us, eventually. And when my guts get ripped out, just so you two know? We're good. Blanket apology, for all the crap that anybody's done, all the way around."
Sam: Some of us pulled a lot of crap, Dean.
Dean: Well, clean slate.
Sam: Okay.
There are obvious differences in context, of course; but on the other hand, I think it's more complicated than I thought at first glance. After everything that's happened in this season around Dean and having a family, a life outside of hunting, I'm no longer sure that speech was as positive as I first thought. Not when you compare it to Salvation. There's a fundamental shift there, and I'm not sure it's one for the best. AND ADDING as I just picked up on it in a comment: Not to mention the specificity of Dean's wording about his death, in this particular speech: his guts ripped out? You mean, like before you went to hell, Dean?
I DON'T KNOW, GUYS. Maybe I am reading too much into this. But Dean's talking about the inevitability of his death, all of their deaths, due to their lives as hunters. I can't really see this as a good sign, even if it's a realistic evaluation of circumstances, and his suggestion of a clean slate is on the balance a good idea. I have thoughts on that too, and why I think blanket apologies/forgiveness might not in the end really work, but this stuff is complicated! I dunno. I think his impulse here is somewhat of a positive step for him, even if he's framing it as "we're all gonna die."
We're back to this, from season 4's "Criss Angel is a Douchebag":
DEAN Man...hope I die before I get old. Whole thing seems brutal, don't it?
SAM You think we will?
DEAN What?
SAM Die before we get old.
DEAN Haven't we both already?
SAM You know what I mean, Dean. I mean, do you think we'll still be chasing demons when we're 60?
DEAN No, I think we'll be dead...for good. What? You want to end up like -- Like travis? Huh?Or Gordon, maybe?
SAM There's Bobby.
DEAN Oh, yeah, there's a poster child for growing old gracefully.
SAM Maybe we'll be different, Dean.
DEAN What kind of Kool-Aid you drinking, man? Sammy, it ends bloody or sad. That's just the life.
And finally, I think it's probably appropriate to close with Rufus's speech from season 3's "Time is On My Side," the last episode before Dean actually does die, and our introduction to Rufus himself:
RUFUS
Kid, can I ask you something?
DEAN
Sure.
RUFUS
You got 3 weeks left. Why you wasting your time chasing after that skinny, stuck-up English girl?
DEAN laughs, but with a measure of discomfort.
DEAN
How’d you know about that?
RUFUS
Because I know things. I know a lot of things about a lot of people.
DEAN
Is that so?
RUFUS
I know aint no pea-shooter gonna save you.
DEAN
What makes you so sure?
RUFUS
Coz that’s the job kid. Even if you managed to scrape out of this one, there’s just gonna be something else down the road. Folks like us, there aint no happy endin’. We all got it comin’.
DEAN
Well, aint you a bucket of sunshine?
RUFUS
I’m what you’ve got to look forward to if you survive. Which you won’t.
I take it back, I have one more piece to close with, from the opener to this current season:
Dean: How long?!
Bobby: All year.
Dean: Oh, you got to be kidding me.
Bobby: And I'd do it again.
Dean: Why?!
Bobby: Because you got out, Dean! You walked away from the life. And I was so damn grateful, you got no idea.
Dean: Do you have any clue what walking away meant for me?
Bobby: Yeah -- a woman and a kid and not getting your guts ripped out at age 30. That's what it meant.
Dean: That woman and that kid -- I went to them because you asked me to.
Bobby: Good.
Dean: Good for who? I showed up on their doorstep half out of my head with grief. God knows why they even let me in. I drank too much. I had nightmares. I looked everywhere. I collected hundreds of books, trying to find anything
to bust you out.
Sam: You promised you'd leave it alone.
Dean: Of course I didn't leave it alone! Sue me! A damn year? You couldn't put me out of my misery?
Bobby: Look, I get it wasn't easy. But that's life! And it's as close to happiness as I've ever seen a hunter get. It ain't like I wanted to lie to you, son. But you were out, Dean.
Dean: Do I look out to you?
eta 2.0: I don't think this is as clear as I'd like it to be, but I'm still struggling to articulate for myself what I'm even trying to get at. I haven't written much (any) meta for this season and it's all kind of jumbled in my head, but I feel like at some point it'll come together!