If you liked
Ore no Imouto ga Konnani Kawaii Wake ga Nai
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...then you might like
Sakura-sou no Pet na Kanojo
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Both have a very similar humor style, though both shows actually have more serious elements to them despite being comedies. Both seem to be a bit more suited to more adult audiences though, if you dont mind a little fanservice and cheeky humor then you cant go wrong with either of these.
Both of these shows have a similar style in humor revolving around a romance based plot. They contain many of the same themes while each remaining unique. In both shows, manga, anime, and games are a major point. If you enjoyed either one of these then give the other a shot.