Yumi is like the only girl that Sensei has sacrificed a significant amount of time helping without receiving sex for it. The main reason initially was probably guilt due to assaulting her, but at this point, Sensei has pointed out that there's something valuable within the relationship as he himself is confused on what he wants the endgame to be.Yumi going to school just to see Akira in detention somewhat draws her even closer to one of my favorites. I'm always debating if I really like her or that i just find her hot, cause she did do a lot of fucked up shit in her bullying (I'll probably reach a conclusion during a replay).
How is it that he saw Niki in Yumi though? I would think that he saw himself instead, since she comes from a broken family where no once cares about her.
If he saw Niki in her, I'd expect that Maya would be at least aware of her existence before the resets but that doesn't seem to be the case. Actually, from their first conversation, it's like Yumi is even doubtful of where Maya came from. Add Pareidolia knowing Yumi by a different name and her having keys to the roof, and maybe there's something there.
Also, since we touched on Maya, new Maya recently said that she has no home but has been with Akira for years. We know she came from somewhere, haven't really talked to him about it either, and ended up living in his rented out tutoring place. So what happened since? He kept renting the place just for her and only stopped when school started?
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She's also one of the girls that he truly feels comfortable with revealing how weak of a person he actually is to. Perhaps the fact that he doesn't feel the need to seduce her, and that she holds no real expectations for him, helps.
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This ties in with several themes of the game. First is love - obviously if your goal from day one is to get in their pants that's kinda a perversion of what love means. Perhaps the fact that he is spending so much time on Yumi (which as mentioned several times in the game is rare since he hates doing anything) without sex as a goal makes it much closer to a real "love" than the other relationships? Or another way to look at it is, since he seems to use sex as a way to connect with (lol) others, is there something he's learning about relationships when he's doing all of this without using sex as a means?
Second is redemption - his chance to significantly improve the life of someone else. Just as he finds meaning in being a father for Ami and improving her life, perhaps there's also meaning in helping Yumi grow as a person outside of just exploiting her vulnerabilities for sex. It's like that story The Spider's Thread - just as the sinner was offered a chance to redeem himself from hell due to the one good thing he's done, Sensei might similarly view this as one of his last chances to become a good person.
The connection with Niki isn't really significant beyond the joke that they're both tsunderes.