Ore no Imouto ga Konnani Kawaii Wake ga Nai., Boku wa Tomodachi ga Sukunai Next Recommendations
Both are the second season, where the male character is surrounded by several females all the time. Both go into some character devolepment (though not very much). There is a similar rivalry between the 2 main female leads: Yozora/Sena and Kuroneko/Kirino.
Blondes, otakus, eroges, same school vibe and shitty endings