Cinderella Boy (2003)

Nobunaga was a teacher who was waiting for that kind of dating sim event to happen in real life. One day, a 14 year old girl named Kicho appears in front of him, saying that she's his wife?! Apparently she came from the Warring States era and seems to have mistaken Nobunaga for the Oda Nobunaga and tells him that she wants to have his children. An age-gap love comedy featuring a teacher with a dating sims brain and a princess with a warring states era brain!!

Stars are everything, granting abilities to Tamers. So when Ivy was born without one, her village took it as an ill omen! Now banished, she leads a lonely life of salvaging rubbish to survive. That is until she befriends Sora, a weak little slime, in the forest. Together, the delicate duo embarks on a heartwarming journey of survival and discovers there’s more to Ivy than being starless.

Trapped in a deadly cursed Mafia game, the students of Yoo-il High must play the game to survive while unraveling the mysteries behind the curse.

Oreimo follows the daily life of an ordinary high school boy named Kyousuke Kousaka. Kyousuke’s younger sister Kirino is a pretty fashion model, but also hides a dark secret of being an otaku of adult games. Kyousuke is the only person to whom Kirino reveals her hidden obsession and other issues.

After dying of overwork in the real world, I’m reincarnated as an immortal witch, and I spend 300 years enjoying a relaxing life. At some point, though, I end up at level 99! All those years spent killing slimes to make the money to pay the bills gave me a ton of experience points. Rumors of the level 99 witch spread, and soon I’m up to my ears in curious adventurers, duelist dragons, and even a monster girl calling me her mom! I’ve never been on an adventure, but I’m the strongest in the world… What’s going to happen to my relaxing life?!

Ichiro Sato is about as average as a student can get... except for his above-average ability to land himself in totally awkward, intensely risqué situations with his no-nonsense teacher, Kana Kojima! Ichiro has his hands full dealing with these steamy shenanigans and unexpected encounters in the most unlikely places. At least it can’t get any worse, right?

There’s something really strange about the maid I just hired! No normal person could be so beautiful, or cook such amazingly delicious food, or know exactly what I want before I even ask. She must be using magic—right, a spell is the only thing that can explain why my chest feels so tight whenever I look at her. I swear, I’m going to get to the bottom of what makes this maid so...mysterious!

After having descended upon this world, the gods have created guilds where adventurers can test their mettle. These guilds, known as "familia," grant adventurers the chance to explore, gather, hunt, or simply enjoy themselves. The Sword Princess, Ais Wallenstein, and the novice mage, Lefiya Viridis, are members of the Loki Familia, who are experts at monster hunting. With the rest of their group, they journey to the tower of Babel in hopes of exploring the dungeon underneath. Home to powerful monsters, the dungeon will fulfill Ais's desire to master her sword skills, while bringing Lefiya closer to her dream of succeeding Riveria Ljos Alf, vice-captain of the Loki Familia, as the most powerful mage in the land.

Set six years prior to the events of Barakamon, detailing the life of Seishuu Handa as a high school student—and a very interesting life it is. In Handa-kun, Seishuu Handa is admired by his peers as a calligraphy genius and given the utmost respect, but Handa-kun himself is under the mistaken impression that the deference and attention he receives from the other students is actually bullying. Handa just wants to live a quiet life, but hilarity ensues as one character after another challenges his position as the school idol, and somehow comes away as a fan all while Handa is horrified and clueless.

The world's most beloved animated characters as precocious preschoolers, discovering the world one baby step at a time.