I feel Destiel in this chili's tonight

Gabriel: “This character suffers from crippling issues with his own self-worth due to a lifetime spent religiously obeying his abusive father!”

Dean: “Oh come on…”

Gabriel: “Final answer?”

Dean: “No uh…Dean. Who is Dean? Me. Whatever.”

Gabriel: “Correct! Nnnnnext category!”

Dean: “…C-character flaws for 200.”

Gabriel: “This character used to consider himself the better of two brothers, but after several years of reckless decisions and huge failings that left hundreds perhaps thousands dead he’s since spiraled into a perpetual state of self-hatred and depression!”

Dean: *side-eyes Sam* “C-can I choose another category?”

Gabriel: “Nope!”

Dean: “But I—“

Gabriel: “Oh come on this one is EASSSYY! I’ll even give you a hint.”

Dean: “No I—“

Gabriel: “It’s the same brother who got your mom kille—”

Dean: “SAM ALRIGHT? SAM. WHO IS SAM?”

Gabriel: “CCCOOOORREECCTTT! AND DEAN IS BLAZING UP THE LEADER BOARD. NNNNEXT QUESTION!”

Dean: *smirks at Sam* Ok, let’s get out of this fucking category.  Sexual Humiliation for 500.

Gabriel: If you’re sure.  “This character tried on panties and he liked it.”

Sam: *buzz* “Who is Dean?”

Gabriel: Right you are my boy. 

Dean: Dammit Sam, how did you know that??

Sam: It was an educated guess.  I’ll take sexual humiliation for 300.

Gabriel: “This character is in love with a certain rebel angel named Castiel and he won’t admit it.“

Castiel: *buzz* “Who is Dean?”

Gabriel: Correctomundo!  I’m surprised you got that, you always were a bit dense bro.

Dean:  CAS?!

Castiel: *squints at board* .. uh.. Betrayal for $100.

(laser beam noises)

Castiel: What-

Gabriel: WOULD YOU LOOK AT THAT IT’S THE DAILY DOUBLE! 

Sam and Dean: *groaning*

Gabriel: How much you wanna wager?

Castiel: Wager? Gambling really isn’t a good habit, and I’m not sure-

Gabriel: All right, the whole $500 it is! “This character betrayed his family for the Winchesters, then betrayed the Winchesters for Crowley, and then, in proper assbutt fashion, betrayed Crowley for himself. And then kind of fucked the world over a few times too, in the meanwhile.”

Castiel: … *heavy sigh* I promised I would redeem myself-

Gabriel: OOPS WRONG ANSWER. We’ll open it to the other contestants. 

Sam: *buzz* Who is Castiel?

Dean: Sammy, come on..

Gabriel: Answer: “While never explained, this fear of Sam Winchester’s has personified multiple times and has caused him to swear off multiple Steven King novels.”

Castiel: *buzz* What is Coulrophobia?

Gabriel: Can I get that in layman’s terms?

Dean: *buzz* What is Sammy’s stupid fear of Clowns?

Gabriel: That is correct, Dean and you have the lead!

Dean: HA! I’ll take Worst Nightmares for Two Hundred!

Gabriel: Answer: “This nearly caused Dean Winchester to run screaming and crying from a wood mill.”

Dean: Oh that’s bull sh-

Sam: *buzz* What is a kitten?

Gabriel: Judges? *Pause* Yes! We’d also have accepted Cat or Feline!

Dean: Oh, Screw you! You wanna play that way, Fine! Sexual humiliation for $400!

Gabriel: Okay! Answer: “Apart from Castiel and Busty Asian Beauties, this has dominated Dean Winchester’s sexual fantasies!”

Dean: “Dude! Come on, what-

Sam: What is the Impala?

Gabriel: Sure thing, Deano, here ya go! “The illegitimate son of John Winchester and Kate Milligan, this twice-dead half-brother of Sam and Dean hasn’t been seen in a hell of a long time.”

Cas: …

Sam: …

Gabriel: You sure baby bro?

Cas: ?–

Gabriel: Alrighty then! Sexual Humiliation for four hundred! He has dreamt many times about Castiel slapping his ass–and doing, ahem, other things–while pretending to do a medical examination on him.

Cas:

Dean: 

Sam:

Cas: Who is Dean Winchester–