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TL;CR
TL;CR MEME
1. Comment with your character.
2. Receive comments from others.
3. Reply to their comments with long ballads and explanations of your characters' relationship throughout the game.
4. Endure everyone else reading your comment like the vultures they are.
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I guess first impressions are just bad? Considering he walked in to Kaoru and Lili fighting over the bed. Kara thought it was astronomically stupid, so his opinion of them both was just. Really bad, lmao. It didn’t help that he learned fast that Kaoru was not a fighter and had very little desire to do much more than gather information? So he decided to never associate with either of them again.
And we saw how well that went!
Well, actually, he did avoid Kaoru for the most part. The only reason his opinion started to improve after a while was that Lili thought so much of him - and, I guess, that he helped Kara find clothes once his usual ones were destroyed. That was helpful, even if he thinks Kaoru went a little overboard?
Then Kaoru decided to meddle. This after Kara had decided he didn’t have a crush on Lili - but when Kaoru explained crushes again, it got more complicated. As a sword, he has a hard enough time understanding normal human emotions, but all these vague definitions of a crush or liking someone made it even harder? But he knew by then how Lili could make things a little too simple at times, just like he does, so he listened to Kaoru and. Well.
Long story short, it’s the shoujo’s fault they started going on dates. Kara doesn’t dislike him for that, and later he came to really appreciate Kaoru for it. And when Lili died, he decided that he would try to protect Koaru as much as he could, because she wouldn’t want anything to happen to her partner.
And Kaoru was also being really emo about the whole thing, so like, mood.
Fast forward a week or two, and he was assigned to kill Kaoru for being corrupted. Kara… wasn’t happy, to say the least. He knew that, in the end, he wouldn’t be able to protect Kaoru forever - but having it happen so soon after they lost Lili kind of really sucked! But by this point, he’d gained a new level of respect for Kaoru’s information gathering skills, so he thought it might be worth it to tell Kaoru beforehand and give him a choice of how he wanted things to go (and also Lili would probably be angry if he didn’t). Since Kara is dedicated to his mission above all else, the most he could do was promise that it would be as quick and painless as he could manage.
He certainly wasn’t expecting Kaoru to have a plan ready? It makes sense, given his apparent skill for getting info and strategizing, and for a kid with no battle experience it wasn’t even a terrible plan. But Kara was also ready to take the fall for killing Kaoru and Squall when it came to trial - not so much for Kaoru to decide that he would be the one protecting Kara. As usual, he didn’t like keeping secrets like this from everyone else - but after seeing what happened to Four, he could see the sense in it, and it was also Kaoru’s choice, so like. He went with it for the kid, more than anything. He’s big on choices, you know.
He did miss Kaoru when he was gone, just a little, and that completely baffled him because they weren’t even that close? Without Lili, Kara isn’t so sure that they would have been allies, in the end. But he’s… pretty grateful that they were, and maybe someday when his war is over, he’ll actually go check on Kaoru in the Ouran world to see how he’s doing - if he really did become as good a strategist as his potential indicated he could be. (Also maybe for romantic advice because he’s the only other human Kara trusts on that.)
But anyway he hopes Kaoru does well in his world, going forward! And if he loses touch with Lili and hurts her feelings somehow, they will be having a Talk. And maybe someday he'll fully explain the whole nonhuman thing too - Kaoru being Japanese means he should know the impact Kara's master had on history, after all, and he trusts the kid not to go around blabbing that he knows one of the swords wielded by Date Masamune.
Kaoru... You're not half bad, kid. Keep it up!