I would have thought Nott would be pushing for Jester to be into Caleb to make him happy, but she encourages Jester with Fjord and then later encourages Beau to act on her crush on Jester (I’m not there yet but I’ve scene the scene).
So either Nott doesn’t know Caleb likes Jester, which it’s not like is overtly obvious because he never intends on acting on it. Or she doesn’t like the idea of Jester with Caleb.
Or she just loves watching all the drama, which might be the most possible.
(Or I just keep watching without speculating without all the facts lol but why would I do that)