 If you liked
Kono Aozora ni Yakusoku wo: Youkoso Tsugumi Ryou e
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 ...then you might like
Amagami SS
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in both series, each of the female characters has their own story arcs. the arcs for the kono aozora female characters are split into 2 parts while in amagami, there are 4 parts, though unlike kono aozora wherein one arc is a continuation from the previous one, the amagami version is more of a what-if scenario if the protagonist chose that heroine
Dealing with girls, problems, and everyday life is not so easy. Both Amagami SS and Kono Aozora ni Yakusoku o features separate arcs featuring a different character whom the main protagonist tries to help. Drama and romance are imminent as the story arcs for both series drags on.