 If you liked
Akachan to Boku
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 ...then you might like
Yuzuki-san Chi no Yonkyoudai.
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It drives the same conflicts of one to no parents in the household, but for akachan to boku has a lot of deeper episodes and at some point will make you cry.
Both anime feature an all-male household going about their daily lives after the loss of one/both parents, and the intimate bond each member of the family has with each other. Yuzuki-san is slightly more comedic throughout, whereas Akachan to Boku has several episodes dealing with serious issues & darker themes, but they're both generally lighthearted family shoujo.