Amagami SS, Kami nomi zo Shiru Sekai II Recommendations
-Both animes's setting/story goes by an omnibus format, and have small arcs that can either or not be diverging from the central plot of the story (with the setting intact)
Involves a somewhat "unhip" male lead who sets out to conquer the love of a new female protagonist. The women each have their own story arc.
There are both light and dramatic moments but overall categorized as a romantic comedy.