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Another "not the best fit" would be Seira Morimura (Princess Nine). Unlike most anime characters she's a toned down expy of a real woman. The real Seira is 6'3" and much more of a delinquent than the 5'7" anime Seira. No, I do not want to know what manner of shenanigans occurred which resulted...

Yomiko is the pretty gal most guys probably wouldn't even bother to try to flirt with because most guys wouldn't even know how to say "hi" to her in a way that doesn't result in her waving them off with "go away, I'm busy".

Yes. First of all, she's actually an adult ... while most anime waifus aren't. Heck, most RL guys would be lucky if they could pry a nerdy bookworm like her away from a library long enough to take her out for dinner and a movie. EDIT: I could probably do it by telling her that I have written...