Hot take maybe but I think Bertie would be FAR more likely to survive the first two months of Dracula than Jeeves would be. Bertie has a healthy sense of self-preservation. Jeeves consistently underestimates how dangerous a situation might get (Steeple Bumpleigh, the club book) because he’s overconfident about his level of control over any given situation. He'd handle Dracula masterfully if they faced off in England, but on Dracula's home turf? Much more doubtful.
I realize this might be a tough sell, so I will explain further (or it's not a tough sell, and I'm going to explain further because I want to). (criteria taken from @canyourfavesurvivecastledracula) Without further ado.
Would Jeeves and Wooster survive Castle Dracula?
Jeeves
Jeeves' survival will depend on how long Dracula finds him more entertaining than irritating. On that basis, I don't think he's long for this world. On the one hand, he has a huge wealth of knowledge about English society and culture that he can recite perfectly from memory. That should buy him at least a little time with noted teaboo Dracula.
On the other hand, he would be absolutely no fun as a vampire plaything. Jeeves cannot be got. Sneaking up on him while he's shaving will yield zero reaction (though that's at least good for his short-term survival--given that, although he DID take the crucifix from the old woman out of politeness, he certainly isn't going to wear it. The rules of fashion don't go out the window just because you're in a spooky castle). Then, although managing the whims of rich jerks is not an insignificant part of a valet's job, Jeeves usually does this by bending his employers to his will. Dracula is not the sort of employer this will work on. It'll just add insult to injury when on top of being impossible to scare, NOW Jeeves is telling Dracula that his favorite cloak is several centuries out of fashion and he's not allowed to wear it anymore.
Jeeves will 100% go exploring in the areas he was told not to go-- though to be fair, he MIGHT actually get away with this, what with his superpower of appearing in rooms without being seen or heard. Said superpower might save him from the brides as well (though this is by no means guaranteed). Since I find it doubtful that Dracula would come to rescue his annoying ass, not being noticed is his best defense.
There are a couple other things working in Jeeves's favor; the question is just whether they'll be enough to save him.
He DOES know shorthand, and could try to send coded letters. He might even have the foresight to squirrel away some extra stationary where Dracula can't find it. But could he get them posted? Would it even do him any good?
He certainly has enough cultural literacy to figure out what his new boss is pretty quickly. If he didn't chuck the crucifix out the carriage window, he might start carrying it around in his pocket.
Psychology of the individual, sure, but the individual in question is a 400-year-old vampire who lives in an isolated castle in a foreign country and is regarded as a terrifying mythological figure in the surrounding villages. Jeeves has never come up against anything this alien before, he's cut off from his normal resources, and opportunities to play people against each other are limited.
He probably has enough upper body strength from all that shrimping and fishing to climb the wall, so he COULD escape if he wanted to, if he survived long enough. It's just, again, that overconfidence, and also Dracula has a vast library full of rare old books that are entirely at his disposal. He's keeping his eyes and ears alert for potential escape strategies, of course, but I don't see him being as desperate to get out as Jonathan was.
There are just a lot of "depends on"s here, and I'm not convinced that luck would shake out in Jeeves's favor, all things considered.
Bertie
Bertie is so perfect for the job of Castle Dracula Prisoner it's like it was made for him. Think about it. Being held against his will in big manor houses comes more naturally to him than breathing. He's afraid of things that are scary. A lifetime of dealing with Aunt Agatha has made him the world's preeminent expert in "curl[ing] up in a ball in the hope that a meek subservience [will] enable [him] to get off lightly." He will NEVER go exploring in places he's been warned away from if nobody is forcing him to (Rev. Aubrey Upjohn's office notwithstanding. There were biscuits in there). He's both fun to talk to and easy to toy with (and extremely English). A+ prisoner. Dracula adores him.
In my opinion, Bertie is at Castle Dracula either because Aunt Agatha got some wires seriously crossed and thinks he’s going to meet an eligible potential bride (I mean, there are certainly brides there), or because Dracula has something Aunt Dahlia wants him to steal (far less likely, given that one of Dracula’s THINGS is famously not owning anything silver). Either way, he's shown himself entirely willing and able to escape down drainpipes if a sitch gets too scaly.
He DOES take the crucifix, and DOES wear it (which is what will save him during the shaving scene, because you KNOW he's going to jump a foot and cut himself like the dickens). He's read enough supernatural goosefleshers to be genre savvy about terrified old women cryptically pushing crucifixes into one's hands. I also think his sunny disposish endeared him to the villagers, and they were particularly vehement about urging him not to go. He doesn't speak German or Romanian, but he's empathetic enough to recognize Pure Terror. So by the time he actually gets to the castle, his imagination is already running wild and he's plenty aware that he is in imminent danger.
I think the biggest risk to Bertie will be the brides; whether or not he's susceptible to trances, if he thinks they're trying to marry him, it's against the code of the Woosters to turn them down. But that only becomes an issue if he comes face to face with them, which, luckily, I think is unlikely on account of the aforementioned "won't go exploring" (and if he did, Dracula would definitely rescue him).
I'm inclined to say due to his drainpipe-escape habits that he WOULD be able to climb the wall and MAY attempt to sneak into Dracula's room to look for the keys if his desperation grows to outweigh his fear. Whether he does or not, though, he does NOT have the stomach to attempt shovel murder, and therefore won't get magic brain fever, and may very well simply walk out the front doors when the people come to take the boxes away. OR he climbs his way out like Jonathan did. Either way.
When Bertie tells this story at the Drones later, Tuppy will say that no doubt it's been greatly exaggerated and all that probably happened was that he spent a couple months in an oldish house entertaining a weird loner.
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Okay I’m not really sure why but I LOVE concepts of like animal courting like male birds doing gorgeous dances and the old stuff where a guy kills a massive animal/predator and presents it to your doorstep like JSJSJWI I giggle and kick my legs at the idea of König killing someone who tried to snipe you and being like “here you go hun :3” or like a medieval AU ghost killing a fucking moose or huge elk for you and showing up with it in his arms RAHH I’d love to hear your thoughts
SKSKSKS I LOVE IT TOO AND I'M NOT ASHAMED TO ADMIT IT
The hunting a big, dangerous predator and presenting it to you screams many of my aus and I could honestly go on for hours about this but for now I'm gonna go with König bringing a whole ass deer back to his cabin deep in the austrian woods where you two are holed up :((
A fearsome soldier and a respected colonel but this man honestly goes kinda dumb for you. Like,, when you're around and there is no one around, just you two in the solitude of the woods in the Alps he really kinda starts thinking not with his rational 'soldier' brain but with his dick and relies more on his more primal hindbrain :((
As far as he knows and cares you two aren't partners but 'mates', and his role as the strong, proud male is to provide for you everything you could want, so warmth, food, comfort, safety and sex :(( Also when you two reside in his cabin? There's gonna be little to no clothes. He has no problem with wearing them obviously and only does this here, but it kinda feels...freeing? And just feels right, plus he gets to show off to you like a proud stallion everything he has, his brawny, strong body and magnificent cock all on display and he's not ashamed. Obviously would never want you to be uncomfortable but if you decide to forgo clothes too he will literally get on his knees and thank you :((
Also, König hunts. His papa took him on many hunting trips when he was a kid so he's a skilled hunter, it's kinda became a necessity living a solitary life like this even before you but when you moved in with him?? He does this not only to put food on the table but also to show off to you like crazy :(( He wants to show you that he's a capable hunter and can provide as a mate for you and any future offspring you may bring into the world ♡
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Currently obsessed with the idea that the boys go to Time for love advice, since "he's married so he knows this stuff right?"
I mean they couldn't recognize a wedding ring??? And neither did he???
And time was saying this in his youth I mean cmon
Twilight: So ancestor. What would you do if like. Malon left to another world and never came back
Time: ... bro Malon called me fairy boy and then we were married like what
Hyrule: So uhh old man. How does one. Meet a girl.
Time: By speaking to her I guess? Or not, Malon did the talking for me
Hyrule: riiiiight...
Wild *no tact*: Hey so like... what if your redheaded wife who's name started with M died.
Time: what?!?!
Wild, undeterred: but like before she proposed.
Time: ...
Wild: and you don't remember if you would have said yes. What's your advice for dealing with that?
Time: ... vent to a fairy?
Warriors: hey old man
Time: no no no not this one asking me please
Warriors: how do I get women to stop coming after me. So I can ya know. Choose without war trying to force me into relationships
Time: I can safely say I've never had that problem captain
Wars: of course not *smirks*
Wars: ok but seriously how do I make them go away
Time: ... wear a wedding ring so they think you're taken, I've got a shiny extra
Time: no no why- they won't stop, I don't know how to do love!
Time: ok well at least I have legend. That kid would never ask for advice, I'll sit by him.
Legend: so old man.
Time, looking forward to a normal conversation: yeah?
Legend: hypothetically, what would you do if you found out Malon didn't exist.
Legend: And her whole world didn't, but it did, and now it doesn't
Time: ...Excuse me for a minute.
Time, writing a letter as fast as he can: MALON HOW DO I GIVE LOVE ADVICE THEY THINK IM WISE
Malon: lol
Happy Valentine's Day guys, have a headcanon :P
The boys go to Time for love advice and Time spouts whatever wise-sounding bs he can, before shoving them all on Malon for therapy when they visit the ranch
Art and comic by Jojo @linkeduniverse! :D
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