Real Anime Situation! DT

First kiss, first date, first real relationship — Shun has a problem. He keeps triggering romance flags and then crushing them in real life, a condition his older sister Mio has started calling Flag Crush Syndrome. Then classmate Ena makes an announcement: she wants to be the leading lady in all of Shun's firsts. They agree to test the curse together and see how far things go. Word spreads. Childhood friend Hinano confesses. So does Ayane, who has always been like a second sister to him. Overnight, Shun's quiet life becomes a battlefield, with three determined women competing for the same heart. He is new to romance in every sense. They are emphatically not.