One thing that gets lost in ship discourse (or its hyper-positive opposite) is that regardless of your feelings on a ship, in order to tell a story, the character relationships do and should have an impact on a character's story arc, and not all relationships are going to offer the same emotional weight throughout any given character's story.
This is particularly true of actual play, wherein each player character is running a separate story as a protagonist, and therefore you have to consider each of them as an individual thread within one larger narrative, on top of the narrative itself.
That being said, the farther you get into the story and the closer to the end you are, the ways those threads can interweave get culled, simply by circumstances. Relationships (platonic, romantic, familial, etc) change over time, and whether they are narratively compelling changes as well. In contrast, "ship" is generally used to suggest a dynamic an individual audience member finds compelling, which may or may not have anything to do with the narrative, even if the dynamic is interesting for reasons of narrative potential (that isn't ultimately explored within canon). These are distinct concepts in terms of analysis. So as a disclaimer, this post is about character relationships within the narrative as it exists—essentially, what makes the story that exists work as well as it does, in the end.
Now that we've got all that out of the way, let's talk about Caleb.
Caleb's problem for much of the campaign is one of survival and self-preservation. His goal is simply to last long enough to find a way to go back in time. Because that is a very open goal, it doesn't inherently have much to tie him to another character in a relationship sense. He is not looking for that, he does not see himself as worthy of it, and it's really not a necessary narrative question, regardless of what attraction he does have.
But over time (and, I would argue, in a way that is fairly singular among the Nein, but I won't get into that here), his priorities begin to shift. Many of his needs are now met in ways that they previously weren't, allowing him to fully consider what he wants. For instance, between the start of the war and the time they reach Xhorhas, he has changed his mind about becoming involved in this war—because he is not being forced into it by possible conscription. He has significantly more options than he did at the start.
What he ends up realizing, as he finds the opportunity to put an end to the war, is that he cannot trust his own judgment. There is near universal support to end the war—even the nations involved are there because of what they view as existential threats. That opinion is not in question. But everything else is. Caleb is a victim of manipulation and brainwashing, and this is very apparent when he starts pleading with the scourger prisoner of war to give him some kind of proof that people like him can change.
And this is not something that anyone else of the Nein can offer him. They can tell him that they think he is a good person and that they trust him, but because of his history—and because he knows how smart he is, and how far he can fall—this isn't something he can take at face value, especially given that they have not seen or known him at his worst, and have not experienced it either.
Yasha may be able to offer some guidance in that area, but she is working through similar issues at both a different pace and in different ways than he is—she isn't seeking any situation where she would make potentially world-shaping decisions or have influence over others like he would. His goals are singularly risky. Veth comes closest to this, in that she very briefly considers prolonging the war to alleviate her own suffering, but it's not a decision she's ever forced to make.
(Honestly, thinking about this, an arc in which Veth does take that deal with Isharnai is a fascinating alternative universe to consider—it would certainly give her the opportunity to relate to Caleb in this way, but it would probably take another fifty episodes before Caleb could even bring himself to consider forgiving her, given it would be in direct conflict to the one thing he's been working at for a third of the campaign up until then. Still, a fascinating consideration!)
So between Caleb attempting to sway the scourger and going to Astrid's house in secret, this is the point at which it seems like the Nein cannot help him do the rest of the work. They have done a lot to get him here and considering what else he wants! But they can't offer him what that is, which is essentially tangible corroboration of what they've already offered.
And at this point in the campaign when taken as a whole, there's only one character who can actually offer that. Because to have real emotional weight, what Caleb is looking for is someone who is as smart as he has, who has made a similarly horrific decision even in spite of that intelligence, and who has now committed to actual change.
It's the commitment to actual change that is difficult, because it requires a support structure—and in hindsight, there's not enough time left to build that up for someone like Astrid or Eadwulf, but it's already partially in place for Essek.
(We can debate all day long about what could've been different if the hiatus never happened, or the campaign had lasted longer, but this is specifically about the campaign that we have. I think there is also an argument to be made that Astrid or Eadwulf would've required a much longer and more intensive timeframe to reach that point even if the campaign had continued than the format really offered, because they have preconceived notions about Caleb that complicates their ability to take what he says at face value even if they care about him succeeding in his goals—but that's also not relevant to this point.)
But I do think this is why Essek progresses very quickly, and is largely committed to aiding them by 124—he already has been aiding them, and has expressed loyalty to them above anyone else.
This is not as much of a leap as it may appear to some, because even by 91 and 97, he had done significant introspection on his own time. This is only a continuation of how he has been characterized thus far. He's expressed doubt from a very early point, whereas Astrid does not begin to express doubt (regardless of whether she feels it, because this is about capacity for willing admittance) until after the dinner with Trent.
What ends up happening is that Essek's the one who actually calls Caleb on things. He gives him an ultimatum with the conversation about Trent when the Nein won't. He offers reason and perspective in the paper room when the rest of the Nein get impatient. He checks off all of the boxes of what Caleb is looking for (which is essentially a narrative mirror), and very early into the Nein's trip through Aeor, Caleb seems to have forgiven him, and his fears and misgivings erode from there.
Only this corroboration, because his opinion of Essek is specifically about his opinion of his own capacity for change, allows him to recognize that returning to the past would simply make him the same person he had been at 17, and finally put that plan, the person that he was, and his parents to rest. If he is not able to be anything other than that boy, then he has no reason to not remain as such, and return to the past; but if he believes himself capable of change, then the question of going back in time is one of leaving behind the person he is now in favor of the boy who made that choice. He is asked, if he believes himself capable of change, to acknowledge that he was that person once, but can now be more than that and move beyond it.
And the proof that he needs in order to affirm that when he is given the opportunity to do so is standing next to him.
Fundamentally, this is not related to Caleb's long-term relationship with Essek at all. This could have been the end of it—they could've parted ways and the story would've still been told and completed.
But I think it is important that a) Essek does get to have some happiness, and b) part of that is with Caleb (though this still doesn't have any bearing on platonic vs romantic, only that they have some kind of close mutual relationship in the long run). On a very basic level, because he is now in this position of being corroborating evidence for Caleb himself, Essek becomes a stand-in for how the narrative sees Caleb, and how Caleb views himself.
If the narrative condemns him and leaves him out to dry, it is an implicit reflection on Caleb—and directly conflicts with the narrative implication that Caleb is not solely worth condemnation. And however much it has nothing to do with romance or a relationship of that kind, Caleb's choice to care about him in the long run is an acknowledgement of being willing to care for and forgive himself.
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i know it's past halloween when i'm posting this, but as a vildia shipper i've been thinking a lot about what vil and idia would do together for halloween--ignoring the existence of the halloween event that we already have--and since i imagine them getting together post-book 6, when ortho has joined the film club and idia is trying to be a better brother to him and be less of a shut-in overall, i think it's a lot of fun to imagine the two of them taking him trick-or-treating!!
i think ortho has tried to get idia to take him trick-or-treating before, but every year idia always says no because he thinks going around to a bunch of rando's houses to get candy is scary, lame, and pointless (they can literally just buy candy at the store, after all!) and he has too many special halloween events to play in his video games anyway. so one day during a film club meeting a few weeks before halloween, ortho offhandedly mentions this, saying he's always wished idia would take him trick-or-treating, and vil decides to talk to idia about it. it actually doesn't take much for idia to agree that yes, it is wrong of him to stay in his room all day when his little brother wants to spend time with him on a holiday, and he absolutely should do it this year, no matter how nervous the thought of it makes him.
he asks vil to come with them, and vil initially says no because as much as he enjoys the aesthetic of halloween, he has a certain reputation and image as a celebrity that does not include doing such childish activities at the age of 18. but idia gets him to change his mind by convincing him that, actually, a lot of his fans would love to see photos and videos of him taking a little kid trick-or-treating because it would be gap moe! a term which vil understands without explanation thanks to idia--and he can see how such a thing just might actually be good for his image, simply by making him seem less otherworldly and unrelatable. so, he agrees, and the three of them spend the next several weeks trying to make their costumes absolutely perfect.
they really go all out, and they have a ton of fun with it. idia's costume has a mask that he keeps on at pretty much all times, so that keeps him from being nearly as nervous as he thought he'd be... except for when ortho gets so excited that he tries to just blast off from house to house without him or vil. but, he and vil both are incredibly happy to see that ortho is so happy, and throughout the night idia's ego gets inflated from all the compliments the three of them get on their costumes, and he and vil constantly exchange snarky comments under their breath about the quality and craftsmanship, or lack thereof, of the costumes and decorations they come across. they collect tons of candy and idia makes sure to add a special attachment to ortho's gear to allow him to actually eat it. vil started thinking he was too old for trick-or-treating a long time ago, but he ends up being pretty glad he went, especially when he sees all of the positive reactions from his fans on magicam.
i also think that before and after the trick-or-treating, ortho would hang out and do halloween stuff with his fellow first years while idia and vil take some time for themselves! the first thing they would do is that idia would introduce vil to one of his favorite survival horror video games, one that has a 2-player co-op mode, and vil might take a bit to get the hang of it but would ultimately really enjoy playing the game with idia.
later at night, they cuddle up and have a bit of a halloween movie marathon. based on idia's love of pumpkin hollow, he's definitely into horror movies, and i also think vil is as well, since he was directing a gothic horror for the film club in silver's PE uniform vignette and then based pomefiore's halloween costumes on gothic horror aesthetics. so, vil would get idia to watch his favorite classic gothic horror film, idia would force vil to watch pumpkin hollow (which vil did not think he would enjoy based on idia's description of its story, but by the end, while he still found it a bit silly, he was able to admire its craftsmanship and creativity and see why idia loved it so much), and then they decide to wind down and watch something more lighthearted. they pick howl's moving castle and idia compares howl to vil several times during the movie, which vil briefly gets annoyed by but then uses as an opportunity to tease idia back.
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