 If you liked
Golden Boy
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 ...then you might like
Kyou kara Ore wa!!
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90's OVA comedy gold. The OVA's are episodic in nature but an overarching plot does flow throughout the entirety of the two shows due to the protagonist(s) goals and their attempts to reach them. Both shows initially appear quite lighthearted but darker themes are touched upon, character development is present and the relationships between characters are decently established.
Overall, Golden Boy and Kyou kara Ore wa!! are just a whole lot of fun to watch. They feature similar art styles, fewer -though lengthier- episodes (GB: 6, KKOW: 10), and conclude with more of an open ending. If you're looking for something new to watch
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Recommended by Nova_Amaya
Both are excellent 90s ova comedies with similar art style.
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Recommended by SlikeDollar