Episode 2: Are You There God?  It's Me, Dean Winchester.
Bobby: I got stacks of lore - biblical, pre-biblical, some of it's in damn Cuniform.   It all says an angel can snatch a soul from the pit.
Dean: What else?
Bobby: What else what?
Dean: What else could do it?
Bobby: Air lift your ass outta the hot box?  As far as I can tell, nothin'.
Sam: Dean, this is good news.
Dean: How?
Sam: Because, for once, this isn't just another round of demon crap.  I mean, maybe you were saved by one of the good guys, you know?
Dean: Okay.  Say, it's true.  Say, there are angels.  I mean that... that totally revolutionizes the sex game.
Sam: What?
Dean: Think about it, Sam.  Castiel was like, flesh and stuff.  I could touch him.  I bang an Angel, I rule the sex game forever.
Sam: Dean...
Dean: No, nothing touches, "I fucked an angel."
Sam: We're talking angels of the lord swooping down from heaven to pull your ass out of hell and you're thinking about the sex game?  Bobby, help me out here.
Bobby:  He's your brother.
 

Episode 3: In the Beginning
Dean: That's not the one you want.
John: Are you following me?
Dean:  No, no, I was just passing by,  I never got to thank you for that cup of coffee this morning.  I was a little out of it.
John: More than a little.
Dean: Let me repay the favor. *eyebrow waggle*
John: What?
Dean: Nothing, I just thought you were gonna... I mean, I set it up for... never mind.  This is the one you want.

and

Deanna: He passed your little pop quiz and now I'm inviting him for dinner.  You hungry?
Dean: Starving.
Deanna: Good.  I'm Deanna, you've met my Husband Samuel.  Now wash up.
Dean: Samuel and... Deanna?
Mary: *nods*
Dean: Really?  Son a bitch was right.  I am the girl.
Mary: What?
Dean: Nothing.

Episode 4: Metamorphosis
Sam: You'll get hungry
Travis: For what?
Dean: Cock.
Travis: What?!
Dean: No, I'm just kidding.  Human flesh.
Sam: Dean, what are you doing?
Dean: I was just trying to soften the blow.
Sam: You know what?  If you can't be serious, you can just go wait in the car.
Dean: Excuse me?
Sam:  You heard me.
Dean: What are you, Dad now?
Sam: Don't start with me...
Travis: Um, I hate to interrupt, but did you say human flesh?
Dean: Yeah, human flesh, long pig, sucks to be you.  Anyway...

Episode 5: Monster
Sam: Revirginate?  I can't even count the number of times we had sex the first night you came back and you're telling you need some blonde floozy waitress in the back of the Impala to consider yourself devirginized?
Dean: It's not the same.  With me and you, it's...
Sam: It's 48 hours is what it was, Dean, and the only time you left the bed was to get the pizza and you didn't even bother to put pants on.
Dean: Well...
Sam: I thought the pizza guy was gonna have a friggin' heart attack.  How does 48 hours not count as devirginized? 
Dean: I already said, it's not the same.
Sam:  By the time we came out, Bobby was blushing.  Bobby, Dean.  The man that got Dad his first tranny was blushing.  Nothing virgin walked out of that room.

Episode 6: Yellow Fever
Sam: Hey, Dean!  I've got something for ya.
Dean: Sam, put that away!
Sam: Come on, baby...
Dean: No!  Get away from me!  You'll split me in two with that thing!
Sam: I'll be gentle.
Dean: No, you won't!

Episode 7: It's the Great Pumpkin, Sam Winchester
Dean: What the hell was that?
Sam: Halloween lore - people used to wear masks to hide from him.  So, I gave it a shot.
Dean: You gave it a shot?
Sam: Yeah, like when you wanted to try anal that first time, only this went much better.
Dean: *glares*

Episode 8: Wishful Thinking
Wess: 'Careful what you wish for.' You know who says that?  Good looking jerks like you guys.  The ones who've got it so easy because you're so handsome.
Sam/Dean: Easy?
Wess: Yeah.  Women... women look at you, right?  They notice you?
Sam: Believe us, we do not have it easy.
Dean: We are miserable.
Sam: I mean, I have to fight tooth and nail just to get this asshole to bottom once a year.
Dean: Oh, yeah?  Well, I gotta put up with this emo bitch just so I can get some regular tail.

Episode 9: I Know What You Did Last Summer
Dean: I guess I, uh.... you know.
Ruby: What?
Dean: I guess I owe you... for Sam.  I just wanna, you know.
Ruby: Don't strain yourself.
Dean: Okay, then.  Is the moment over?  Good, cause that was awkward.
Ruby: Besides, not like I did anything you wouldn't do.  Which, by that way, didn't leave out a whole lot.
Dean:  ....Sam, can I shoot her yet?

Episode 10: Heaven and Hell
Dean:  Dude.
Sam:  Don't even say it, Dean.
Dean:  No, no.  Just, you know, score, like, a zillion for me.
Sam:  Right.
Dean:  And you?  You get negative for coma girl.

Episode 11: Family Remains
Dean: Wait, why kill herself after the baby?
Sam: Maybe because her dad called her a dirty little whore and said he was gonna lock the baby up where nobody could ever see it?
Dean:  Why would he say that?
*Sam and Dean exchange several looks*
Dean: Oh, gross.
Sam: Pot, kettle, black, Dean.
Dean: Yeah, but I never knocked you up.  Totally different.

Episode 12: Criss Angel Is A Douche Bag
Dean: Sam, we've got a problem.
Sam: What?  Dean, what are you doing here?  I thought you were supposed to be meeting with that Chief dude.
Dean:  That's it, Sam, that's the problem.
Sam: I don't understand.
Dean:  It's Kripke.
Sam: Huh?
Dean: He's trying to kill the fangirls again.  I went to that address and it turns out The Chief was a leather daddy with a whip.
Sam: What?!
Dean: Yeah, and the worst part?  He asked me my safe word.
Sam: That cheap bastard.  We don't use safe words.
Dean: I know!
Sam: ... Did you ask if you could borrow the whip?

Episode 13: Afterschool Special
*on watching the flashbacks*
Dean: I don't remember you being that short.
Sam: What does it matter?
Dean: Well, I... I mean, I kind of feel like a pedophile now, or something.
Sam: We were only four years apart.
Dean: Four years and like three feet.
Sam: Maybe I should start feeling bad then.
Dean: How come?
Sam: 'Cause I'm fucking a midget.
Dean: Sasquatch.

and

Dean: Hey, that teacher is encouraging you!
Sam: He's helping me.
Dean: Whatever.  Is that why you went to Stanford?
Sam: ...
Dean: It is, isn't it?  That was some big turning point for you - when some asshole teacher told you that being yourself was more important than family.  Where are my keys?
Sam: Why?
Dean: I'll be back in an hour.
Sam: Dean, where are you going?
Dean: I've got an ass to kick!

Episode 14: Sex and Violence
Dean: You gonna say goodbye to Kara?
Sam: Nah, not interested.
Dean: Yeah, probably a good idea.  Although...
Sam: What?
Dean: You sure she's human?  I mean, she did survived your magic death penis.
Sam: Would you stop calling it that?  I've had sex with you and Ruby and you're both still around.
Dean: I died and went to hell, the fact that I came back is inconsequential, and Ruby is a walking corpse, so she doesn't count.
Sam: You are such a jerk.
Dean: Bitch.

Episode 15: Death Takes a Holiday
*jogger runs through them*
Dean: Woh! *puts his arm inside Sam's chest*
Sam: ...
Dean: Am I making you uncomfortable?
Sam: Get out of me.
Dean: ...do you want to take this one, or should I?
Sam: Oh, for the love of... go ahead, take your shot.
Dean: Nah, it's too easy.  Come on, prude.
Sam: *mumbles*  You're not a prude if you put out.

Episode 16:  On the Head of a Pin
Alastair: Oh, go ahead, send me back.  If you can.
Sam: I'm stronger than that now.  Now I can kill.
Sam: *kills Alistair*
Castiel: *gives Sam the I-am-strangely-turned-on-by-that look*
Sam:  *gives Castiel the up-and-down*  Later.

Episode 17: It's a Terrible Life
Dean: So, what?  I'm just hallucinating all this, is that it?
Zachariah:  Not at all.  Real place, real haunting.  Just plunked you in the middle without the benefit of your memories.
Dean: Just to shake things up? Hm? So, you guys can have fun watching us run around like ass clowns in... in... in monkey suits?  Where's Sam?  I need to wash the gay off me.
Zachariah: You intend to 'wash the gay off' by sleeping with your brother?
Dean: Hey, I may have been making it with a dude, but I was still a man.  I can taste soy, you angelic bastard.