Negima! Magister Negi Magi (TV)
Season 1 - 10-year old Negi Springfield is a wizard-in-training, and needs only to pass one more test in order to become a Master Wizard. Unfortunately, his final task is a bizarre one- to become a English teacher at an all-females boarding school. As soon as he arrives, he completely embarasses one of his students, Asuna Kagurazaka, and replaces the teacher she loves, which garners her hatred. To make matters worse, Asuna learns that Negi is a wizard,and promises to tell unless he helps her out. But, unfortunately, circumstances force them to work together to do many things, from fighting evil wizards to helping the class pass their final exam, with a lot of humor, magic, and romances thrown in.
OVA - Sometime after all the events which took place during Negi's first year as a teacher, Class 2-A goes on a school trip to a beautiful island for Spring break. Everything is fine now, but troubles continue for Negi, because he's still the main atraction of the class. But he has something else to worry about, Asuna is angry at him because he told her she had nothing to do with his studies as a wizard. During the trip, the situation gets intense as Asuna's friends try to help Negi make up with her.
Season 2 - Negi Springfield has graduated from magic school and is sent off to Japan to further his studies. He becomes the homeroom/english teacher at an exclusive private school and has run-ins with an enemy of his father, as well as with Asuna, who makes his life a living hell, and that's before she discovers his secret. He learns about (and from) his students and about himself in order to become a master mage, like his father before him.