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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Misfortune Teller
tldr: An older Danny, apprentice to Clockwork, does a lot of field work across dimensions, resetting the timeline, queuing future events, and who knows what else. Occasionally, he warns people about such upcoming possibilities, to set them on the right path. How, you might ask? Well in this case... as a wandering fortune teller.
Crack-fic (oh god, it's getting long and my logic brain won't let it remain as crack) where Danny becomes Clockwork's apprentice after getting his GED. Living his infinite afterlife to the fullest. Inspired by this tumblr post.
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Working for Clockwork had been... interesting so far. At first, Danny got frustrated by how vague and cryptic Clockwork was. He'd just shunt Danny off to some ancient time with a few words, his own time medallion (Danny carried it everywhere with him now), and then pop back into the portal, leaving Danny with only the faintest idea of where to go.
Eventually, after enough time (ha!) spent around Clockwork, Danny figured out that it just basically meant that he had free reign and to do whatever he wanted. Because if he went on the wrong path, (like that one time in Pompeii when he had almost caused the volcano to explode a few years too early), Clockwork would just pop on by, say another few cryptic words, and then it'd all be fine and dandy, or as he liked to say, "All is as it should be... Now stop practicing your wail by an active volcano."
After telling Jazz about that (it was supposed to be funny, not concerning), she just sighed and shook her head, with a forlorn "think before you act, Danny!" but hey, it'd turned out fine so far, so who cares how he does what Clockwork asks him to do, as long as it gets done, right? Even if it's with a liiiiitle more mischief than strictly required.
Besides. Danny was the one who had been doing time shenanigans across millennia, not Jazz. And he thought he'd been getting pretty good at it too! He'd actually started giving himself a different made-up background for each universe he visited. Sam and Tucker were helping him keep up with the identities on a spreadsheet, so if he had to go back to one he'd already visited, he'd remember who he'd said he was supposed to be.
---
He was on a call with them one evening while haunting Jazz's apartment, doing just that, when he felt a familiar tingle in the back of his throat, as well as a heightened awareness of the seconds passing by, that always accompanied his mentor's appearance.
Sam was talking about his past stint posing as a god of death when he cut in. "Hey- sorry to interrupt, Sam- Clocky's here, guys, I gotta dip."
"Aw, come on! We hardly talked any this past week since you passed your certifications, man," Tucker complained.
Danny rubbed the back of his neck sheepishly. "Yeah, yeah. Partly on you too though, you've been caught up outside of class, and Sam's schedule is nearly the opposite of yours."
Sam hummed in agreement despiter Tucker's scoff.
Danny missed hanging out with them as much as they had in high school, but hey, life goes on. Or at least, theirs did, to college. After finally flunking out of Casper High, he'd taken some time to get used to his responsibilities in the ghost zone, and when he had, he realized that he didn't really have much enthusiasm or timeleft for his human life.
And he didn't really want to go back home either.
But Jazz had made him tie up any loose ends before he noped-off to god knows where, which frankly, he had to thank her for. Getting his GED took a few years, but it was an accomplishment that could be attributed to Danny Fenton, no ghostliness required. Then he was able to let that tether go free.
Pulled out of his musings by a few more grumbles from Tucker, Danny said his goodbyes, promising to call the next time they were all available.
After hanging up, Danny swiveled around, anticipation already lighting up his eyes an ethereal green.
Clockwork, for his part, had been waiting patiently through Danny's lengthy goodbyes. Although he supposed that it tracked for the watcher of time to be patient. With his job, it'd be a nightmare if he wasn't.
"Phantom," Clockwork spoke, calm as always. "I have some tasks I need you to complete as my apprentice."
And Danny, always ready for adventure, didn't need him to explain any further. "Sure! When do you need me to be?"
Clockwork smiled at that. "I am fortunate you are eager. Follow me."
---
Danny popped into existence in this universe with a burst of cold air and static electricity. He found himself hovering by a clocktower above a sprawling, gothic city. Smog and light pollution obscured the stars above him, to his disappointment. He comforted himself with the fact that he'd probably have all the time he wanted to fly someplace less populated to see them later.
He started off by familiarizing himself with the city. As he flew, he followed the trail of power and met the resident city-spirit, a spooky- but kind underneath- woman draped in black lace, who told him her name was Gotham. He spoke in length with her about this universe, its heroes, and her knights. On that, she was very enthusiastic... or at least Danny thought she was, her projected emotions belaying much more than her gloomy exterior. She told him how her knights had been through a lot and would need some guidance fighting the darkness that pooled in her deepest corners, smiling with too much glee, filling lungs with fear, and terrorizing with cold hard bullets.
Danny could sense that the dangers she spoke of were growing in power, ever slowly. The longer they shadowed people's minds and hearts, an intangible thing grew that lent them more otherworldly pull than their physical forms had right to hold.
That must be what he was sent here for.
But... they were weak, pitifully so for him, infinite king as he was. And besides, he wasn't here in that sense. He was a messenger, a simple apprentice. And he could do this however he wanted.
Cue his talk with Lady Gotham, and subsequent idea to arm her knights. With what? Well, he figured knowledge would be a start. Flying high above the city invisibly, Danny noticed a sea of colors and lights by what appeared to be the city's pier. He flew down, noting that it appeared to be the setup spot for a travelling circus or carnival of some kind.
He considered what to do. One of Lady Gotham's troubles was a madman clown, right? Well maybe he'd be attracted to his ilk here... and with the danger came the knights. Maybe he could catch one of them here?
Danny was floating around at the entrance and beginning to formulate a plan when a flyer caught his eye. Looking for a mystic to read fortunes. URGENT!
Hadn't Clockwork said something about fortunes? And he hadn't made an identity in this universe yet...
A mischievous smile crept across Danny's face, splitting it in two with far too many teeth.
---
Half a city away, a man in all black, perched on the very same clocktower that Phantom had Appeared by, shivered as he felt an ominous premonition about his sanity in the near future...
Said man quickly opened his comms to check in with his many, many kids. Yet even after hearing back from each, he still felt apprehensive.
Somewhere even further, Clockwork laughed.
---
And that's how Danny found himself seated at a fortune teller's booth at a pier in Gotham, two days later, for the Tricksy Traveling Circus's grand opening.
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