Mama wa Shougaku 4-nensei

Both animes are family centred and the main characters are middle schoolers, who raise a child. I watched both animes as a kid and I felt quite nostalgic after rewatching them again - that's why I've decided to recommend them to you guys!! Oh and did I mention that both animes have the 90's style?! ;)) Short summary of each anime and how they're quite similar: Akachan to Boku is more about an older brother raising his little brother after their mother passed away whereas Mama wa Shougaku 4 Nensei is about a baby, Mirai, who time traveled back in time to her mother, who is still in middle school. Natsumi, the main characters name, has to raise Mirai until they figure out how to return her back to the future. Gosh both animes are adorable and show how important family is and even friends!! (Friendships in both animes play a major role as well ´^`). They're both wholesome animes with great songs too D:> I HIGHLY RECOMMEND!!  read more 

An older child is taking care of a much younger child. They both share comedic and dramatic moments revolved around this similarity. 

A baby suddenly appears and young girl has to take on the mother role and take care of it. Both are shoujo comedies.