I'll Make a Habit of It (1994)

Shion and Rui are the dream team when it comes to hitting on women. Tonight was going to be another night of hooking up with girls for Shion, but he ended up taking a strange drug. When he woke up... he'd turned into a girl?! Rui came looking for Shion, but didn't recognize him, and started hitting on him...

The story follows Hime Arikawa, whose absent parents have left him saddled with a huge debt. After being saved from debt collectors by three girls on the student council, in exchange for paying off his debt, he agrees to spend the rest of his high school career dressed as a girl.

16-year-old Hayate is really down on his luck. Because his unemployed parents are good-for-nothings who waste what money they have on gambling, Hayate had to start working at a young age to help out his family. Although such experience has made him inhumanly fast and tough and skilled at things boys aren't normally skilled at, it has also left him in an awkward position, as his parents have racked up such a huge gambling debt that they have sold Hayate to the yakuza for the value of his organs. In a desperate attempt to avoid that fate, Hayate decides to become a "bad guy" and kidnap someone to be held for ransom, but his efforts to do so are mistaken as a confession of love by the girl he targets. When he helps save the (as it turns out) ultra-wealthy 13-year-old Nagi from real kidnappers, she takes him in and gives him a job as her new personal butler (and love interest) until he can pay off his debt. But Hayate is more attracted to Nagi's beautiful teenage maid Maria, and head butler Klaus is initially disapproving of a boy with such a poor look. And then there's Nagi's pet Tama, who is also a force to be reckoned with.

Misaki Ayuzawa is the first female student council president at a once all-boys school turned co-ed. She rules the school with strict discipline demeanor. But she has a secret, she works at a maid cafe due to her families circumstances. One day the popular A-student and notorious heart breaker Takumi Usui finds out her secret and makes a deal with her to keep it hush from the school in exchange for spending some time with him.

Sakamachi Kinjiro discovers that the most popular student in their school, Subaru Konoe—the butler of the headmaster’s daughter, Kanade Suzutsuki—is actually a girl.

Eiichirō Maruo (nicknamed "Ei-chan" for his grades being straight "A") is an honor student, bookworm, and is not interested in anything other than studying. In order to solve his problem of lacking physical strength, he enrolled a tennis school and soon found the fascinating side of tennis. Being a tennis newbie lacking physical strength, he supplement his shortcomings with his excellent observing and analyzing skills.

The story begins with Oomiya Shinobu, a 15-year-old, seemingly pure Japanese girl who actually did a homestay in Great Britain. Even after coming back to Japan, she still misses her time overseas. One day, an airmail letter arrives from Alice, the girl in Shinobu's host family in Great Britain. The letter reads: Shinobu, I'm coming to Japan! The Japanese/British girls' mixed comedy follows the lives of Shinobu, Alice, and other girls from both Japan and Great Britain.

Miyamo Chio, a first-year at the completely ordinary high school Samejima Academy. Chio just wants to get through her school life without standing out too much, but for some reason, all kinds of obstacles await her along the path she takes to school. Her long-time friend Nonomura Manana, who's trying to quit being an otaku; the flawless Hosokawa Yuki, who occupies the top caste in the school; and lots of nameless people about town find themselves in Chio's path as she employs the (useless) techniques she's acquired from her Western video games in her daily efforts to get to school.

Kintaro Oe is a 25-year-old boy who left Tokyo University and now lives a simple life, traveling by bicycle to learn everything he can about the world.

The incidents which occurred on August 14th and 15th bring a group of young boys and girls together… They are members of a group they call themselves the "Mekakushi Dan" (Blindfold Organization) and each member possesses a strange power involving their eyes.