Hear me out, Shadowgast and Widomauk shippers: Caleb has two hands and past experience with threesomes.
Sorry, Beau is taken.
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Essek, saying goodbye to the Nein in 141: Maybe [I’ll] spend some time in Uthodurn. I hear the cupcakes are quite good there.
So here’s the thing - Jester gave Essek a black moss cupcake in ep 74. That’s just under half the campaign ago, and almost five months of in-universe time. And Essek… remembered it, fondly, all that time.
Looking back, I think the cupcake scene might actually be one of the first moments when one of the Nein breaks through to Essek. This is before Caleb and Essek’s second dunamancy bonding session, before ‘we are friends now’ ‘I like that’. Jester says she’s got a present for Essek, he gives a sarcastic little ‘yay’… and then she brings out a cupcake, and Essek’s constant little smile drops. He spends almost ten seconds examining the cupcake, staring at it from every angle.
And… it’s pretty obvious that no one gets the Shadowhand a cupcake. No one in the Dynasty passes a bakery and goes ‘oh, those cakes look nice, I’ll get one for Essek. You know, Essek, the Shadowhand, son of Umavi Thelyss, the guy who sits at the right hand of the Bright Queen. Essek, the untouchable dunamancy prodigy who bends gravity and time to his will. Essek who everyone in the Dynasty’s mildly terrified of. That Essek.’
But Jester did exactly that. Because she’s Jester. Because the Nein treat Essek as a person, not as the Shadowhand, for probably the first time in his life. (And yes, they also enjoy ruffling his feathers - but honestly, I think that’s part of it. When has anyone ever ruffled Essek’s feathers rather than treating him as the Untouchable Shadowhand tm?)
Essek’s already bonded with the Nein a bit, of course - but even the dunamancy lessons are something that Caleb’s doing for his own agenda. Jester’s hug, early on, was as much a prank as a thanks. But this? This is Jester doing something just to be nice. For all we know, it’s the first time in Essek’s life that anyone has done something just to be nice to him.
Of course he remembered it, so many months later. Of course he couldn’t leave the Grove without subtly telling Jester, ‘hey, I remember that. Thank you.’
Tl;dr: Gee, Jester, how come your Archfey lets you have two antagonists who became your friends because you gave them a cupcake?