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Well, I do feel the need to clarify something.
I mean of course, there are things that Issei could have done differently. I just really hope to whatever god runs this anime universe, that Rias will have her own epiphany.
I mean her mother did try to hint to her that she was doing it wrong.
I know this might sound really weird, but despite her literally throwing herself at Issei, I really do not feel like she has made her feelings clear enough.
We are talking about a boy who lives in a very complicated situation. He lives in a very strange world where every female he meets ends up hungering for his D, and while he does not seem mind this, I don't think he really understands how to treat everyone other than just "showing them kindness".
Not only that, but in the case of Rias, she is not just his club president, she is the younger sister of the current ruler of the underworld. And he is currently her soldier slash bodyguard. She is someone he admires. Not just as a woman, but as a person. I'm not sure whether Rias understands that if she wants him to call her by her name, she needs to make him feel like it's safe for him to do so.
Her question of "What am I to you?", when put in a vacuum, is actually an incredibly vague question. Of course it might seem more specific when you put it in context, but it's the context right now which is unclear. She, and probably most viewers, see it in the context of "do you see me as someone you want to have an intimate relationship with?" or perhaps even "Am I more special to you than everyone here?" (hint, the answer would have been yes if she just asked that question straight). But that would fail to take into account all of Issei's own experiences and emotions. It fails to take into account the fact that Issei is intimidated by both her status and frankly, being the typical woman most would view as "out of their league".
It takes two to tango, Rias.
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