Ore no Kanojo to Osananajimi ga Shuraba Sugiru (Oreshura) follows Eita Kidou, a high school student who wants nothing to do with romance. After the infidelity of his parents tears his family apart, he becomes deeply skeptical of love and spends his entire high school life focused on his studies in order to become a doctor.
That resolve is quickly challenged when the beautiful and popular Masuzu Natsukawa notices Eita's apathy. Tired of being the object of other people's affection, she asks him to pretend to be her boyfriend, since she is also disgusted by the notion of love. Eita refuses, but Masuzu has one trick left up her sleeve: she has Eita’s journal and threatens to post the embarrassing contents online if he does not comply.
Soon, Eita is trapped in a fake romance with the most desired girl at school, and his quiet life is turned upside down. Envy from his peers, unexpected confessions, and the pressure of maintaining the act force him to cope with a relationship he never wanted and all the trouble that comes with it.