Jester's existence is hidden from the rest of the world, and she spends much of her childhood alone in a room. she's just a daughter of the coast-famous courtesan; and if it gets out that a coast-famous courtesan has a child, well— that's the end of that career.

that said — while she's hidden, nothing is hidden from her. Jester has a very clear idea of who her mother is, what she does, and the fact that she's good at it. she grows up without the taboo of sex, but with an understanding of how to read people, how to keep them company. above all— she knows that she is loved by her mother; and knows if anyone tries to tell her otherwise, they simply don't know what they're talking about. still, the most important take away is that she grows up alone.

the good news is that she can't miss what she's never had; the bad news is that while she reads people better than she lets on, while she can empathize with someone she barely knows, that's the extent of her social graces ( but more on that later ).

one day, the Traveler visits her; then comes back, day after day. a magical, hooded figure that suddenly appears in her room to teach her magic and keep her company when her mother cannot ( only when her mother cannot ) — what's not to love? young, impressionable, gullible Jester adores him on sight. he's funny, he's cool, he's powerful, and most importantly he calls her his favorite ( and for someone who has only grown up with the affections of her mother, those words are powerful ).

they make a — promise, of sorts. for all the magic that he teaches her, she'll do her best to make sure more people learn about how great he is. spread the influence of the Traveler by playing tricks on the unsuspecting, disrupt the way things are. make people's lives a little more spontaneous, escalate with an easy "yes, and" to absolutely everything. it's an excellent promise in Jester's eyes, just a little more incentive to live the life she already leads; so she accepts. and from that point forward, she and the Traveler are the best of friends. and while she meets many, many people that quickly become her friend, she's ready to leave them at a moment's notice if it's for the mysterious figure in the green cloak.

( but for a cleric of of the Traveler, Jester definitely doesn't like healing. )

speaking of meeting a lot of people—

the long and short of it is that Jester plays a prank that goes too far, and now she's wanted in the city that she's called home her entire life. she takes this brand-new exile as an opportunity to look for her long-last dad. while it kickstarts a lot of things, it's the next thing that's a little more important:

she meets a half-orc who is fascinated by all the super cool magic she has, along with a little magic of his own. he mentions that he's looking to go to the heart of the Empire to learn a bit more about his new magic, and Jester is nothing if easily distracted. so she meets her very first ( mortal ) friend.

while Fjord may never be as great as the Traveler, Jester still loves him dearly; she accepts him with little condition ( though to be fair, she doesn't have a whole lot of conditions in the first place ). except — the title of the very first friend is something she unconsciously puts a lot of weight on. she's grown up as the sole receiver of any attention from her mother and Traveler, so some part of her expects the same from Fjord.

which is to say — while she's confident and sociable, she's not too different than a child learning how to form relationships for the first time. she's intensely possessive of the people she cares about; her mother, the Traveler, Fjord, and the rest of the Mighty Nein, once she meets them. it's all in different ways — sadness when Beau looks like she's ready to ditch their roommate arrangement, envious fury when someone begins to flirt heavily with Fjord, devastation when it looks like the Traveler doesn't speak to her regularly. some of Jester's best traits are from the childish wonder she harbors in everything she does, but that same childishness breeds some of her ugliest traits, too.

here's the thing: she quickly gets branded a weirdo from the moment she meets the rest of the Mighty Nein, but it's that same quirkiness that has this shady group of assholes warm up to her the fastest. they're not good people, none of them are, with their headstrong ideas and vices and histories, but they manage to find company in each other.

unfortunately, it's not always perfect.

for context: Jester expects a package from her mother, filled with funds for her trip ( since her initial sum had been spent immediately ). given the distance between her home and her current location, it doesn't arrive as soon as she'd expect them to. unsurprisingly, this is absolutely devastating.

again — Jester, for as quickly as she can empathize with situations she's familiar with, she's absolutely awful at understanding anything that's not. she doesn't have the experience to understand why her being frustrated for not being handed a large sum of money is ... unbelievable to someone like Caleb. and it's the misunderstanding that has her say some pretty insensitive things. it's not a pretty fight — because with the childishness comes the stubbornness — but this is the first time she really shows her capacity to grow.

she's upset when Caleb storms off. she apologizes the next time she gets the chance to speak to him, and tries to be a little smarter with her money ( just a little; she's still excited by the most ridiculous of things, and will always turn a blind eye to getting scammed if it means it'll be fun ). it takes something explosive and dramatic before the lesson goes through ( over something that's relatively minor, let's be honest ), but the important thing is that it happens.

( or specifically, what happens after. )

getting kidnapped by a bunch of traffickers should be a traumatic experience. while the rest of the party scrambles to find them, they can all think of one thing; Fjord and Yasha will be fine, but Jester?

the kick is that Jester is the least affected.

she springs up right away from the little cell she's been kept in; immediately begins to chat away about how she and Fjord were making eyes all night at each other. the party finds it unsettling, but to Jester? it's just how Jester is. she feels abandoned by the Traveler, her friend is dead, and she's gone through what is easily the worst thing in her life — but from that comes an extreme desire to make sure everyone else is happy.

it's important to mention this isn't martyrdom; Jester has no interest in sacrificing herself for the sake of others. she really is just acting the way she'd normally act. she knows, by acting her regular, upbeat self, she's able to instill a sense of normalcy in the party; and she needs that to work in order to cope ( and that's probably the most unsettling bit of all ).

a floating, spiritual lollipop that lasts for about a minute. the lollipop has movement independent of jesters to a certain degree, but it can only be controlled within her line of sight. the official D&D ruling is that the weapon will deal more damage when casted at higher levels, but I'd like to imagine it lasts longer the more powerful she gets, as well!