I just thought of this, it was such a small thing in the early days of The Nien, Caleb reading smut right? He said it was because he found Magic Tomes in a sex-book shop but there is evidence in him reading all of Tusk Love that he genuinely enjoys a little romance novel on occasion.
We also know that in The Tower, every book he has ever read is in the library, there for Beauregard and Jester have probably spent at least one night in The Tower combing through the romance novels to find the dirtiest one to embrace Caleb with.
Jester: *in a dramatic Zeminman accent* Oh Professor Hemlock your lesson on Hold Person was very insightful perhaps I could have a private lesson?
Beauregard: *pretentious man voice* It would be a pleasure to tutor you on the many uses of Hold Person.
Caleb: *beet red* Y-you two are pricks
Kingsley: I’m sure you know plenty about the subject Professor
i just... it's so important to remember that Jester and Fjord are not actually pirates.
Kingsley is a pirate, but Jester and Fjord run a completely legitimate company and own a small fleet of totally above-board merchant vessels.
Fjord is dressed like that entirely for the aesthetic. Because he likes it, and he knows he looks good, and he knows that Jester likes it, and he's comfortable being like "yeah I'm gonna dress sexy for my super hot girlfriend and i don't care if people stare at me!" Insecurity time over, time for Admiral Tusktooth now!!!