 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
Gi(a)rlish Number
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Both are created by the same author so they have clear similarities. They both have witty characters and almost always have something satirical to say about anime, life, culture, relationships, exc. Both draw their roots from light novels so the dialogue is very dense, and have lot of meaning to them that one cannot will miss if they gloss over it.
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Recommended by reluctantbeeswax
Both are by the same light novel author, Watari Watanabe, and put darker and realistic spins on the teenage romcom genre and the anime industry respectively. Hikki and Chitose both share a fair few character traits, and a brother-sister-like relationship are in both.
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Recommended by ButadonMeitantei