Free to Be You and Me (5.03)

Gotta love how hellers completely ignore when the SAME reference is made by Dean himself about wincest:

Just My Imagination (11.08)

11.07, Plush.

Sam: So um, on the off chance You're actually listening. I gotta be real honest, the visions aren't making a whole lot of real sense to me. Truth is, I don't know what's what. Please, what are You trying to say? [...] Dean: I thought we talked about this. Sam: Yeah, we did, Dean. But why's it so hard to believe God could be sending me visions about the Darkness? Dean: You kidding me? He didn't feel the need to show up for the Apocalypse, why would He give a crap now?

Ah, yes, the God Foreshadowing in s11... and yeah, Sam's visions were super confusing because they were coming from Lucifer, not God, back in early s11, but hooboy does this sound prophetic for s14, too?

Dean: I'm saying don't count on God, count on us.

In an episode filled with "masks" and "clowns" and Sam visually "trapped in a cage with a clown," all of this was indeed "you're being tricked by Lucifer" foreshadowing, but isn't that just what Chuck has been doing to them all along?

11.08, Just My Imagination.

Another hint to Sam's sometimes shaky connection with reality, and his willingness to believe SOMETIMES panning out, but other times literally becoming a trap for him. Like what happens to him in the very next episode...

11.09, O Brother Where Art Thou?

Thou art being deceived by your personal archnemeses... Dean by Amara, Sam by Lucifer...

Little, heartbroken Sam, and then adult heartbroken Sam. Sully, always checking up on Sam even after all those years. Like, my heart. The writers have literally fucking killed me. 

Delivery Service

The thing is, Dean's a complete pushover when it comes to kids.

The night air is cold and unfriendly, especially since Dean's jeans are wet up to the thigh--and Sam's too, but Sam functions like a walking furnace most of the time, so he probably doesn't even notice. Dean notices, but he's still somewhat caught up in trying to process what the hell just happened.

"I think that might seriously be the weirdest thing we've ever killed." He's probably never going to be able to look the Teenage Ninja Mutant Turtles in the eye again.

Free to Be You and Me (5.03)

HELLERS: Destiel is SOOOOOOOO canon!!!!!!!

US: Is it?

Hellers must have turned off the episode after this scene, THINKING/IMAGINING/DELUDING THEMSELVES that Dean was going to have sex with him, otherwise how did they miss what actually happened?

Dean took him to a brothel and got him a FEMALE hooker to sleep with.

While we are on the subject of 'Bert and Ernie':

Just My Imagination (11.08)

and

Mint Condition (14.04)