I think Caleb should kind of fall on his face trying to woo Mollymauk in the lead up to his inheriting his dead brother's seat. Like, he's got the spirit, but not the drive, and he can't execute.
Sees a beautiful man and is like would you be entertained by a fey familiar of your own? And Molly is like, sure! Do I have to feed it? And Caleb is like, no. And then Mollymauk mostly uses it for fun displays at parties until he kind of forgets to ever summon it (the familiar is fine with this tbh).
Meanwhile Yasha walks in late to Molly's birthday and is like still grimy from the road (she's been out for a while) and she's like let's have everyone go out into the garden for a last toast, and when the party gets out there there's like a gorgeous young adult tree she somenow managed to have transported so it could be on their estate (from a place Molly misses traveling through when they were nobodies), and a ton of exotic flowers ready to plant on the morrow. Plus, like, two huge tamed wolves that she hands the leashes for to Molly.
Jester to Caleb where they're hanging back in the crowd like "sorry, man I don't think you had a chance, that's on me"