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If you liked Tearmoon Teikoku Monogatari: Dantoudai kara Hajimaru, Hime no Tensei Gyakuten Story add

...then you might like Higeki no Genkyou to Naru Saikyou Gedou Last Boss Joou wa Tami no Tame ni Tsukushimasu. add

Both show a similar plot where the MC tries to become a better person when they are given a second chance.

If you liked Gakuen Babysitters add

...then you might like Yuzuki-san Chi no Yonkyoudai. add

These two anime series center on brothers who have lost both of their parents. Both of these anime kept me around because of the brothers' close bond and intense affection for one another.