Then, too, at sea—to use a homely but expressive phrase—you miss a man so much. A dozen men are shut up together in a little bark, upon the wide, wide sea, and for months and months see no forms and hear no voices but their own, and one is taken suddenly from among them, and they miss him at every turn. It is like losing a limb. There are no new faces or new scenes to fill up the gap. There is always an empty berth in the forecastle, and one man wanting when the small night watch is mustered. There is one less to take up the wheel, and one less to lay out with you upon the yard. You miss his form, and the sound of his voice, for habit had made them almost necessary to you, and each of your senses feels the loss.
—a sailor's diary entry, on losing a shipmate, ca. 1834 (from Two Years Before the Mast by Richard Henry Dana Jr.)
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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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On a very stupid note, can you imagine how embarrassing it is for Bruce Wayne, the most paranoid and secretive man on earth, that whenever there's drama in his family it inevitably reaches a significant portion of the superhero community?
And he can't even go after any one person, because Alfred would tell Dick (who tells Wally and Donna, especially if it was really stupid), Steph would tell Kara (who would tell Clark, who would tell Diana, who already knew via Donna), and Tim would tell Kon, Damian would tell Jon and Connor, Duke tells Jason about it, and because Wally told Barry Hal now knows (and other Lanterns), J'onn knew because Bruce was fuming and Clark was trying to figure out how to bring it up, Cass told Dinah and Barbara so now the entirety of the Arrowfam and Birds of Prey know too and so on.
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