Skinner & Chalmers - Hotel Room (Patreon)

I fucking can't get enough of these two. Ever since childhood I have been rooting for these idiots to get together. Yes, they have a very toxic, sometimes tender, always unreasonable relationship but it gives me life. Their feelings towards one another have always been far too strong and enigmatic to just be... I dunno, platonic. There's also that one episode where he's worried about Skinner and when he finds out he's okay has this quiet moment with him where he says, 'Don't ever do that again.' (scare him) and for me that was always the most clear indicator of their true feelings. For Skinner's part, he is always trying to make Chalmers proud, find him capable, worthy, dare I say appealing? This is the longest 'will they or won't they?' relationship I've ever been so invested in.

They've gone on work trips together in canon, and I don't find it a stretch to think of Chalmers 'accidentally' leaving the bathroom door open in their hotel room to give Skinner just a taste of what the poor man has been fantasizing about for years. And honestly, that kind of power move seems like just the kind of thing both of them would be into. For the younger or unfamiliar folks, this is Superintendent Gary Chalmers and Principal Seymour Skinner from the Simpsons. Also have an edit where they both have mustaches because, I am who I am and I know what I like!