Cas: …Dean?

Dean: Hey Cas so it seems you might have asked me out?

Cas: What? Auuugh just forget I said any -

Dean: No - Listen. Uh - if - uh - look. I like you.

Cas: Uh.. …. What?


look at these assholes


Dean: Ugh! I can’t believe I left my clothes…I liked that jacket…

Sam: Dean! Dean! Are you okay?! I was really worried and I felt so bad I’m sor -

Dean: It was just a bad day Sammy. It’s okay. … ‘Sides, I went home with this gorgeous woman - huuuuge brea -

Sam: Okay,get your dirty sex hands off of me. … Better get to the hangar or Bobby’ll have your head!

Benny: You slept with him, didn’t you?

Dean: No, WORSE. I cried and told him too much and he fuckin’ spooned me in his sleep and he doesn’t remember it and I fuckin’ made him breakfast and shit. Benny, I think I love him.

Benny: Oh, you poor soul.


dean is just a big loser


Cas: Thanks for picking me up on such short notice, Jimmy.

Jimmy: You got called in, on your day off, to do do physical labor why are you in such a hurry?

Cas: Oh, no reason - extra mon -

Jimmy: You’re excited to watch Dean lift things, aren’t you.

Cas: Don’t judge me.

Jimmy: ASK HIM OUT Jesus, I’m getting a divorce and I’m better at this than you.


just to kind of put a cap on jimmy and cas’s convo

cas hung up the phone forcefully when “going out” came up and then five minutes later had to call jimmy back to ask for a ride

jimmy thinks his life was simpler without a brother. boring. but simpler.


this happened awhile back, when they first started hanging out.

dean loves benny a lot, maybe is attracted to him if you get him drunk enough to admit it, but it mostly comes down to just mutually caring about each other a lot. 

when dean truly cares about someone, you’d be hard pressed to ever get him to admit it without his inhibitions being down in some way. random flings are easier than actually developing a relationship because there’s so much room for getting hurt in that scenario.

benny doesn’t go out with anyone, and never talks about his love life.


Dean: Hey Cas, I know I kind of ran out this morning but…Thanks. After how I came over…you could have just kicked me out.

Cas: No problem, Dean…anytime, really. …. So uh, would that be a first date, or…?

Dean: SERIOUSLY? I’m being open with you and - can’t you just like - UGH - WHATEVER. And Sammy says I’m allergic to feelings. Just ONCE I’d like to - UGH.

Cas: Dean - I - I…I was being…… …. … shit.


well, cas, you tried

Dean: Oh no! Benny! Benny, you gotta help me! It’s been years since -

Benny: Look Freckles, you’re cute and hopeless but this is heavy.

Dean: I don’t even know his favorite color - what if I only like him because he bugs me??

Benny: I will drop this on you.


benny doesn’t know why they’re friends


Gabriel: If you take a picture, it’ll last longer Cassie

Cas: You know my phone doesn’t - shut up.

Gabriel: So that’s not his favorite shirt you’re wearing?

Cas: What?! Uh - no - no - of course not ; (thinking) Shit - must have - dammit


cas maybe you should pay attention to what shirt you grab from the random articles of clothing on your floor next time

or you could clean

also, good job gabriel, you’ve been carrying the same small box back and forth from the plane to the truck for the past hour you are working very hard