If you liked
Ore no Imouto ga Konnani Kawaii Wake ga Nai
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...then you might like
Kokoro Connect
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There's a certain uncomfortable frankness in both of these series. It's not necessarily unpleasant - the series are so candid that awkwardness naturally follows, and that can be charming in its own way. The awkwardness is often played for humour, and the candidness creates some touching moments.
Oreimo focuses more on humour while Kokoro Connect focuses more on drama, but comedy and drama are important aspects of both series.
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