S2, R2, B1:

• I am so proud of you: I don't know if I'll ever be over this line. We shall see.
• Enabling your sick habit: Same reason as round 1--I love well-fed hedonist Dean.
• Let me help a little bit: I assume I'm going to be the minority on this one, but it screams S5 to me, and that is ♥
• I enjoy sunsets: Sassy!Dean for the win. And I don't mean that Sassy.

S2, R2, B2:

• I had one job and I screwed it up: Just a powerhouse of writing and delivery.
• Just one part worth saving: Vote for the car people. It saved the world. I'm tellin' ya.
• I kept you alive for some reason: Ah, YED, you totally shouldn't have.
• You're bossy...and short: Shaddup, Sasquatch. But you're cute.

What were the other occasions?

Finding Andy's bong in Simon Says, and mentioning listening to Dark Side of the Moon while watching The Wizard of Oz in Dream a Little Dream of Me.

And in today's episode, when Sam asks him in the art room if it brings back memories (of being in high school), Dean sees the kid putting the giant bong in the kiln and says, "That brings back memories."

And it does strike me funny. Dean kicking back with a twelve-pack is one thing, doing shots or playing quarters or whatever, but sitting around getting stoned? Just doesn't seem like Dean, except in a "I'll try anything hedonistic once" way.

I don't imagine Dean off his game much. And fighting drunk is easier than fighting stoned.

Argh! You seeded some of my favorite lines against each other! This was hard.

S2, R2, B1

• Dean, I'm sorry: seminal, will never not love this
• Sick habit: the essence of brotherly love, really
• I should have stayed dead: oh, DEAN
• Aquarius: what's not to love about Dean?

S2, R2, B2

• What am I supposed to do?: live, Dean, just live
• I think I'm adorable: Dean/Henrikson 4Evah!
• Bitch/jerk fumble: who is Dean, if not Sam's brother?
• Bossy and short: drunk Sam will never not be funny

This round is going to go ALL WRONG. I can feel it.

This round is TOO HARD. I will have to think on it and vote later.

And fighting drunk is easier than fighting stoned.

That's what I mean! The writers think the offhand remarks are funny, and they are, but they're a bit OOC.

I can't vote yet. Must think.

Bracket #1

• Proud John – no contest
• I eat – love Dean and all his sick habits
• Stayed dead – woobie Dean over awesome Sam (this was tough)
• Aquarius Dean – smart aleck Dean over weak gay joke

Bracket #2

• What am I supposed to do? – this one true quote all the way
• Impala/Dean worth saving – yes they are
• sacrificing Dean – feh I want the other quote to go down
• bossy…short – bad drunk acting Jared FTW

Season 2, Round 2, Bracket #1/2: Planes/Clowns--This is one of the top 3 quotes that gets stuck in my head from the show.

Lab rat.

Never should have come back.

Aquarius. Both of these were fairly "meh" for me, so I won't be sad to see one go in the next round, too.

Season 2, Round 2, Bracket #2/2:

What's dead should stay dead. Apparently, I strongly prefer pithy.

Adorable

Bitch/Jerk. This one was tough. But it's not just how Winchesters say "I love you" but also point to how much Dean hangs on that relationship.

Bossy

I don't think they're out of character. I expect during his occasional breaks (like the one where he met Lisa), Dean indulged in a little relaxation.

I think it's because although we've seen him drink so heavily we haven't seen him drunk or hungover (unlike Sam)

We've seen him hungover at least once (Provenance, I believe), and possibly twice, depending on how you read the opening scene with Sam and Dean in Jump the Shark.