 If you liked
Ore no Imouto ga Konnani Kawaii Wake ga Nai
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 ...then you might like
Sasami-san@Ganbaranai
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Both anime have a lot of fun characters, including older brothers who look after their little sisters! OreImo references a lot of otaku culture whilst Sasami-san (while doing that as well) mainly references Japanese mythology, but I think Sasami-san is thematically close enough to OreImo that every OreImo fan should give it a shot.
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Recommended by Jaehaerys48