deancasheadcanons:

Sam takes a deep breath and begins to type.

Recipient: Charlie Bradbury

So I owe you 10 bucks.

Dang. I wanted my 50. Do I owe you anything?

Nah, I was way off. The only way you’d owe me anything is if they told me themselves, which they didn’t. 

You walk in on a BJ or something?

…Or something.

Recipient: Scottish Douchebag

You owe me 20.

Bloody hell, they couldn’t wait until December? 

I told you it would happen soon.

Recipient: Jody Mills

We split, so we don’t owe each other anything.

Wait, in which direction? 

Cas initiated, so that was my $40. It took two weeks before I noticed, so that’s your $40.

Damn. Tell them I said congratulations.

Recipient: Claire Novak

Remind me to give you $200 next time I see you.

Lol sucks to suck, dude.

You’ve been around for FIVE MINUTES, how did you know?

I calls ‘em as I sees ‘em….also, I told Cas to go for it.

Cheater.

Recipient: Dean Winchester

I’m going to the store. You need anything? Beer? Candles? Lube?

Yeah, all that would be great. Make sure you get Astroglide. It feels the nicest on Cas’ fingers.

Can we not.

It’s a natural act, Sammy.

Can. We. Not.

So, how much money did you lose?

I have no idea what you’re talking about.

Sure you don’t.