Where does it first happen, Perkins?
Some more S5:
5x20: Crowley: Where's your moose?
5x17: Castiel's voicemail: You have reached the voice mail of [Castiel: I don’t understand. Why do you want me to say my name?]
5x20: Dean: All those angels, all those demons, all those sons of bitches, they just don't get it, do they Sammy?
Sam: No they don't, Dean.
Dean: You see, Brady, we're the ones you should be afraid of.
There's the one from Dream a Little Dream
Dean: Bitch.
Sam: What?
Dean: uh... you're supposed to say jerk.
That's from What Is and What Should Never Be, isn't it, Laga?
eta: supernaturalwiki has it like this:
Dean: Bitch.
Sam: What are you calling me a bitch for?
Dean: You're supposed to say jerk.
Sam: What?
Where does it first happen, Perkins?
I don't know. I will try to find out though.
First "bitch, jerk" is in the pilot in John's motel room.
That's my other problem- trying to remember exact quotes. I found this exchange on imdb
5x14
Dean: This is a fight? Are we in a fight?
Castiel: This is... their handshake.
Dean: I don't like it!
Castiel: No one likes it.
S4 4x2 Castiel: You should show me some respect. I dragged you out of hell. I can throw you back in.
I'll just be over here with the other herded cats.
S1 Ep1 Dean: Whoa, easy, tiger.
S1 Ep1 Sam: We got work to do.
S1 Ep2 Dean: But see, my mom - I know she wanted me to be brave. I think about that every day. And I do my best to be brave.
S1 Ep5 Dean: (to his Dad's voicemail) Dad, I know I've left messages before. I don't even know if you get 'em. But I'm with Sam and we're in Lawrence and there's something in our old house. I don't know if it's the thing that killed Mom or not... but... (tears up) I don't know what to do. So whatever you're doing, if you could get here... please. I need your help, Dad.
S1 Ep6: Sam: I miss conversations that didn't start with "this killer truck."
The first bitch, jerk was right after, "No chick flick moments" in the pilot.