 If you liked
Ookami to Koushinryou II
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 ...then you might like
Honzuki no Gekokujou: Shisho ni Naru Tame ni wa Shudan wo Erandeiraremasen
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Each entertain with drama and comedy relief, while also surrounding its story's respective characters and plot points among microeconomic concepts, game theory, innovation, or entrepreneurship, in a pre-Renaissance European-type setting. Dialogue-heavy and rich in commentary about human psychology, the two anime offer a lot of substance in terms of character interaction, and will please those who muster the patience for slow-burning (but ultimately rewarding) productions.
If you enjoyed the intellectualism of Spice and Wolf, then you'll be in good company when watching Ascendance of a Bookworm.
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Recommended by FluffyFlareon