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If you liked Ore no Imouto ga Konnani Kawaii Wake ga Nai add

...then you might like Imouto ga Oshisugiru! add

Both Oreimo and Imouto ga Oshisugiru feature a tsundere gyaru female protagonist that's the younger sibling of the male protagonist who's secretly an otaku. Unlike Oreimo though Imouto ga Oshisugiru's female protagonist is a direct fan of the male protagonist without realizing it (since he's a mangaka) rather than a bishoujo game otaku imposing her interests onto the male protagonist. Similar to Oreimo though, both siblings learn to reconnect through shared interests and goals and also feature some(?) romantic tension.

If you liked Iyagatteru Kimi ga Suki add

...then you might like Kitanai Kimi ga Ichiban Kawaii add

Both Iyagatteru Kimi ga Suki and Kitanai Kimi ga Ichiban Kawaii feature a protagonist who enjoys humilating their partner through various kinds of fetish play. The female MC in Iyagatteru Kimi ga Suki for the most part outright despises it, while the (other) female MC in Kitanai Kimi ga Ichiban Kawaii embraces it. Also there's both diaper scenes (that's not a spoiler that's a fact) for some reason??

If you liked Gunslinger Girl add

...then you might like Dívčí Válka add

Both series have a focus on a young female protagonist(s) fighting against a large antagonistic group and their primary weapons are firearms, and a very large cast of characters. The focus is somewhat similar in the sense that all the fights are politically driven, and each fight is shown to have a lot of strategic prep work beforehand, along with the fights being much more grounded in reality, no fancy shonen powerups or whatever. If you enjoyed those aspects of Dívčí Válka you would enjoy Gunslinger Girl just as much.