Dean: On a scale of one to ten, how bad is it?
Sam: I'd say.... arrestable.

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@piesaltcoffee
Dean: On a scale of one to ten, how bad is it?
Sam: I'd say.... arrestable.
Dean: If I die again, delete my search history.
Sam: If you die again, I'm posting it.
Sam: Why are you carrying a ladder..?
Dean: I'm emotionally preparing for my next bad decision.
Cas: Be honest.
Dean: Oh no.
Dean: Cas and I are dating!
Sam: Yeah, I know.
Dean: How? I only asked him yesterday.
Sam: What the fuck were you doing before that then?
Dean: Cas, you love me right?
Cas: Normally, I'd say yes without hesitation, but I feel like this is going somewhere I don't like.
Cas: I don't think anyone will ever be truly in love with me.
Dean: Are you sure?
Cas: Yes.
Dean, aggressively pointing at himself: Are you fucking sure?!
Sam: So, when are we going to tell him?
Dean: Just give him a minute.
Cas: *Pulling a door that clearly says push*
Dean, storms into the hotel room: Ok, which one of you idiots put a curse doughnut in the fridge??
Sam: What??
Dean: I took ONE bite and suddenly I could hear the thoughts of every squirrel in a 10 mile radius.
Cas: I thought you liked doughnuts.
Dean: Not when they tell me my "Aura is mediocre" Cas!!
Sam: Why are you soaking wet??
Dean: I tried to summon a minor water spirit.
Sam: And?
Dean: Turns out it was actually a VERY major water spirit.
Castiel, dripping: It threw him into the river.
Dean: You let it!!
Cas: You told me to "let you handle it"
Dean: I LIED!!
Crowley: I am the King of Hell. Fear me.
Jack: Do you want a Capri sun?
Crowley: ....
Crowley, sighing: Tangerine, if you have it.
Sam: The next person who says "It can't get any worse" is responsible for whatever happens next.
Dean: It can't get any worse.
Sam: DEAN!
*Ceiling collapses*
Dean: ....
Dean: Ok, my bad.
Gabriel: I came because I sensed a disturbance in the force.
Sam: Uh, wh-
Dean: No, keep going. This is the most helpful he's ever been.
Rowena: I brought snacks!
Sam: Great!
Dean: Wait, are they cursed snacks?
Rowena, offended gasp: How dare you??
Sam: ....
Dean: ....
Rowena: ....
Rowena: Only the nachos..
Bobby: I leave for two hours and y'all summon another ancient god?!
Sam: He followed us home. We didn't summon him.
Dean: He likes cheeseburgers.
Ancient god: I like cheeseburgers.
Sam: "This place is ancient, dangerous, and full of traps."
Dean: "Cool. Love that for us."
Sam: "Dean, think before you act."
Dean: "I did think."
Sam: "And?"
Dean: "I thought, "this is a terrible idea", and then I did it anyway."