Title Recommendations based on Cloud Strife

At an elite, old-fashioned boarding school in New England, a passionate English teacher inspires his students to rebel against convention and seize the potential of every day, courting the disdain of the stern headmaster.

Otis Milburn is near the bottom of the social totem pole in high school. After Otis realizes he's quite good at giving sex advice, he and his friend Mae Wiley team up to charge students for sex therapy.