 If you liked
Maison Ikkoku
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 ...then you might like
High Score Girl
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Both have timid but realistic main character that fall in love with a girl that seems to be way out of they league, in both you see support character trying to steam up the romance because in booth animes the couples are too timid, the main women of both animes haves strong motives to be timid, i also in both animes you see time passing, i give a 10/10 for both.
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Recommended by GuilhermeRibeiro