 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
Masamune-kun no Revenge
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Both have a mean yet admirable lead female.
Similar outcast characters trying to fit in.
Slice of life\ Drama
Both have deep plots and characters.
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Recommended by OhsnapitsDavid
In both anime, the main female protagonists can not express their feelings, but in the end they get what they feel. The boys, on the other hand, can not see the feelings of Adagaki and Yukinoshita. As the story unfolds, however, this situation changes. The feelings of both sides are slowly reaching each other.
Both shows appear and can be labelled as 'cliche' school-set rom-coms (emphasis on 'can') where the MC smarter than the regular MC. However, Masamune is about the popular students while Oregairu is about the not-popular students.
Also, traps.
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Recommended by ButadonMeitantei
If you like how Cold Hearted Yukino was , then you might wanna check Aki from Masamune-kun no Revenge ...