 If you liked
Eromanga-sensei
|
 ...then you might like
Ryuuou no Oshigoto!
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Both are ecchi comedies with a significant amount of the main heroines being of a problematic age. While Eromanga is ostensibly about a slightly older high school student writing novels with his younger sister illustrator, Ryuuou no Oshigoto is about an older male Shogi master taking on a younger female apprentice.
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Recommended by AgentI9029