Yeah, Dean does say something to Gabe about "oh you think killing me is funny" or whatever. I think Dean remembers Sam *telling* him about dying over and over - when they wake up on the last Wednesday (the one with the giant hug), Dean's like, dude how many Tuesdays did you live through? And Sam says something like Enough. So we have on-screen interaction to confirm that Dean would sass Gabe about killing him a lot, but nothing where Sam explicitly tells him about those months where Dean was dead - I don't think it comes up later?? Anyway, since they had Sam specifically evade telling Dean about the months and months of Tuesdays afterwards, I think we're supposed to leave the ep with that impression that Sam hides what happened from Dean.

But yes, this: Probably they'd play it to each other as a pain in the ass than a really painful thing. Totally.

LOLOL I would love Dean laughing at his deaths in Mystery Spot. Like, at first he's affronted when Sam tells him what happens (YOU PEED YOURSELF. ... OF COURSE I PEED MYSELF). And then he's like, electric razor? tacos?? falling furniture what even lololol