Dean: You guys don't walk enough. You're gonna get flabby. You know, I'm starting to think Junkless has a better sense of humor than you do.
Castiel: Uriel's the funniest angel in the garrison. Ask anyone.

Castiel: I know our fate rests with you.
Dean: Then you guys are screwed. I can't do it, Cass, it's too big. Alastair was right. I'm not a hero, I'm not strong enough. Well I guess I'm not the man either of our dads wanted me to be. Find someone else. It's not me.

I couldn't break him, pulled out all the stops, but John, he was made of something unique. The stuff of heroes. But then came Dean. Dean Winchester, I thought I was up against it again. But, daddy's little girl, he broke. He broke in thirty. Just not the man your daddy wanted you to be, huh, Dean?

Alastair

Castiel: You need to be more careful.
Dean: You need to learn how to manage a damn devil's trap.

Supernatural Season 4 Episode 16 Quotes

Castiel: You need to be more careful.
Dean: You need to learn how to manage a damn devil's trap.

I couldn't break him, pulled out all the stops, but John, he was made of something unique. The stuff of heroes. But then came Dean. Dean Winchester, I thought I was up against it again. But, daddy's little girl, he broke. He broke in thirty. Just not the man your daddy wanted you to be, huh, Dean?

Alastair