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The Doctor chose Nearl as their secretary out of a precautionary measure- Someone who's not involved with his past, could protect him (if need be), skilled in various fields, and also had some baggage of her own.
Of course, after Nearl decides to remain in Kazimierz, it's probably... Amiya? Good presenting face, strong chemistry. Everyone likes her.
For Dr. Llewellyn, there's not an Operator that resembles Alice yet - and she didn't have anyone assigned as personal guards so it prompted her to arrange Ash and Oda for those roles. After some time and the occassional self-doubting at 3am, the Lupo got the duo to take on further secretarial duties so that she will have an easier time processing the Rhodes Island that she woke up to.
Now before those two joined, Dr. Llewellyn's first ever assistant was Lappland - a fellow Lupo like her, despite their differing humor styles and backgrounds. If anything, Llewellyn doesn't mind putting up with the other Lupo's antics.
iserlohn does not have an assistant technically because of his calculation abilities and also because kaltsit originally thought it too dangerous to leave a terran in the same room as a technical alien, so he's worked without an assistant since the beginning and doesn't see the need to have one. phantom is more formally his bodyguard and is tasked to protect him, any additional secretary work done on top of that is entirely voluntary LOL
Sanguine's first secretary/assistant was Eyjafjalla. She was one of his patients he had really close bond with, so he wanted to keep an eye on her condition throughout the day. She was also one of the people who were willing to not judge him based on his actions in Babel. Though she also proved herself to be very capable in this role
His second and current assistant is obviously Skadi and is a lot more complex to explain. Long story short, after a bit of a turbulent start, they slowly started trusting each other more and more, in large part due to them often sharing a drink at the bar and somewhere in the middle of it all he asked her to become his bodyguard/assistant. After some hesitation from our favourite bounty hunter (and frankly quite a bit of convincing), Skadi eventually agreed. And the rest is history, as we all know what happened with time~
Interloper chose Pallas as his secretary for two reasons. The first is his social skills are horrid and he's so bad at talking to people younger than him, so he was able to vibe with Pallas pretty quick. They bonded a lot over drinking and sharing stories of their lives or heroic tales they heard. The second is that she serves as his personal trainer when it comes to physical fitness so he can become less of a lame old man. Mostly however he just REALLY needs someone to talk to or else all the paperwork will make him pass out from boredom.
gravel is still willing to become the doctor's personal guard even after shes hired as an operator at rhodes island and since there are little to no threat at the landship she started assisting them w day to day tasks and projects. then the doctor asked gravel is she wants to officially become their secretary in which of course she agrees
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