This is so long overdue.
KAITO'S CURRENT ROMANTIC CONFLICTS, NOW IN ESSAY FORM 8Db
For being such a flirt and a pervert, Kaito pretty much sucks with girls and actual relationships. In my opinion, he has gone on dates and held hands and has even kissed his fair share of girls in his time, but all of these were short little flings, and none of these women were really able to keep his attention. Therefore, Kaito has never really, honestly dated someone before. He's okay with this! His approach to romance is pretty casual; if there's a girl he likes, then hurrah! If not, OH WELL, no harm done, just gonna keep bouncing around, bouncing around--
Where he is right now, however... his whole 'casual approach' to romance and dating kind of isn't cutting it.
Kaito is attracted to strong-willed girls, the kind who are independent and tough and yes, this means the kind that are most likely to punch him in the fact whenever he says something they may not like. Banter is a plus! As is someone who would be likely to humor him whenever he is pulling a prank or generally doing something childishly stupid. It also helps if said girl can balance out his chaotic personality a bit, and reel him in when he gets a little too out there. Obviously this is not a rigid I ONLY DATE GIRLS OF THIS TYPE thing, but it's generally what he unconsciously looks for in a partner.
Heather, everyone's favorite monster ass-kicking Silent Hill protagonist, fits this description very well. Those two really hit it off from pretty much their first conversation, with Kaito being a dork and telling spooky-yet-silly ghost stories and Heather humoring him and teasing him about it while he did so. From the moment they both revealed they were dorks who had no problem with giving each other silly nicknames (Awesome-san and Smiley) while talking about the silliest things, it was pretty clear they were going to become friends, which... they did! They bonded over their similar senses of humor, and for Kaito, Heather kind of became that witty banter buddy he could always count on to make him grin from over the Pokegear.
The first time they really got close was during the nightmare fog hallucination event. Kaito had to relive being chased by Snake all over again while thinking most of the people he cared about were dead, so it was understandable that afterward he turned to his friends to make sure they were okay (Kaito really, really hates losing people). Kaito and Heather both have the tendency to try to smile and joke through their trauma, which is one reason he went to her since she handles things in nearly the same way as him. This was the first time Heather came clean to Kaito about parts of Silent Hill, and... in return (and prompted by his previous confessions to Kay and Johan on the matter, which helped him feel a bit more comfortable with doing this) he told her about Kaitou Kid and his dad. The fact that she was understanding and didn't scold him for it was something he really appreciated, and... after that, he really came to appreciate her not only as a friend he could joke around with, but as a friend he could really trust. And from there, their continued interactions have prompted a steadily growing friendship based on mutual trust, understanding, and empathy.
All of this is why, yes, Kaito really likes Heather in that 'more than a friend' way. I don't think I can really pinpoint when he started liking her in that way, but I know he didn't really realize it until Kay and Johan disappeared from Johto and, in her attempts to console him, she told him she loved him. He knows she meant it in a platonic manner, but it still made him stop, do a double-take, and realize that he was blushing when she said it. It was the first time Kaito ever really thought of Heather in a more-than-friends way. It was abrupt, but honest, and he found he didn't really mind it so much.
SO WHAT IS THE PROBLEM, THEN?
... well the problem is, Heather isn't the only girl he feels this way about. Not that he would admit this so easily, though.
Aoko is Kaito's best friend! He's know her the longest out of all of his pals and has come to really care for her deeply. Sure, he picks on her and teases her and calls her names, but it's in that... little kid pulling the pigtails of the girl he really likes way (which is so mature I know cry). Aoko really gets him in a way similar to Heather, probably because she has known him for so long and has seen him at his most vulnerable (i.e. when his dad died). She has just always been... there for him when he needed her, and she also never fails to bring a smile to his face whenever they banter. Aoko may not know about Kid like Heather does so she may not be able to empathize with that part of him, but the only reason he doesn't tell her about Kid is because he's really nervous that it'll chase her off (he is the big bad thief in white who tears her father away from her, after all). Aoko's friendship is too important to him to risk losing, so he keeps quiet. It makes him feel guilty-- really guilty, actually-- but for now, that's the way things have to be. He'd really like to tell her one day (it would be a great relief if he could), but he is just... waiting for the right moment. The moment when she won't punch him in the face.
Despite being close to her, Kaito never really thought of Aoko in a romantic sense before Johto, either. Like... if asked what she was to him, he would have just said that she is VERY IMPORTANT and left it at that. He got a lot of teasing from his classmates about his relationship with her, with several of them jokingly calling her his 'girlfriend,' but he pretty much brushed all of this off and never let it get to him. Rise and to a degree Crow have pretty much kept up the tradition of teasing Kaito about his status with Aoko, but just like at home, he just brushes this stuff off and calls them crazy. Aoko is not his girlfriend damn it she is just his friends CAN'T A GUY BE FRIENDS WITH A GIRL AND NOT BE BOTHERED ABOUT IT GEEZ.
And then fourth wall happened. And fourth wall Hakuba poked and pried and somehow, mostly by being a smarmy bastard and making Kaito jealous, got him to admit that... just maybe, underneath all of that banter and teasing, he really cared about Aoko more than he would a regular friend. In this conversation, Kaito basically said that the reason he didn't... go to Aoko with this was because he was trying to keep her as detached from his life as Kid as possible due to the liabilities that come with it, in which Hakuba pointed out that if Kaito remained detached for too long, he'd lose her. And probably really hurt her in the process. Naturally, this stirred up Kaito's ever-present guilt, to the point of where he honestly wasn't sure how to respond. While Kaito doesn't remember this conversation, any and all latent emotion Hakuba stirred up during it remained once the fourth wall event was over. And ever since then, Kaito hasn't been able to look at Aoko without going "I wonder..."
This... very clearly, inspires much conflict. Because now there are two girls he really cares about, but since he is such a DORK when it comes to actual emotion, he isn't quite sure how to proceed. SO WHAT IS HE GOING TO DO ABOUT IT?
NOTHING.
Because that is obviously the best solution! Since Kaito really is in a state of confusion about all of this and honestly has no idea how to handle it, he just figures it'd be better to not address it. Heather and Aoko are both incredibly important to him, and that is that. Teasing him about Aoko will pretty much still make him grump and deny any and all romantic possibilities. He has not been teased about Heather yet, but doing the same with her might get him to internally flail a bit while also denying that she is more than a friend. He really doesn't like not knowing what to do in this situation, so... part of him hopes that if he pretends everything is okay a solution will present itself. It isn't like him to not be proactive about things (he's an actor, and he prefers to do something first rather than wait), but in a situation where he isn't sure how to proceed and where he knows one of the parties could be hurt, it's... really the only choice he has. It doesn't help that he actually isn't sure how Aoko and Heather feel in return, which is just an even bigger reason for him to stay quiet. He doesn't want to make either friendship awkward, after all.
It should be noted that while Kaito does think of both Heather and Aoko in that way, there is kind of a difference in the way he sees them. Heather is a close friend, someone he can empathize with and someone he cares about deeply. But although he does like her in a more-than-friends way, it is still only 'like.' Meanwhile, his feelings for Aoko run a bit... deeper than that. This is mostly because he has had more than a year with Aoko, more time to really get to know her and come to care about her. The way he feels about her is more akin to 'love,' though he still has yet to make that connection in his mind. Whether this difference will have an affect on how he proceeds, I have no idea! Especially since he isn't. Planning on doing anything about this anytime soon. Sob.
It should also be noted that Kaito will probably always love Aoko, no matter what happens. She is that important to him after all. She is also the first girl he has ever felt that strongly about (even if he wasn't aware of it for most of the time), and you never really, truly forget about your first love. :(
BASICALLY Kaito is a bit confused and honestly has no idea what to do about it, so he's doing what he does best: shoving everything deep down inside of him and proceeding with a poker face as although nothing is wrong.
This will not backfire. He is sure of it. |D