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Josephine Bolton, an 8th grader at Saint Agnes Academy, secretly dates Dean Jefferson Brant, the school's charming 40-year-old dean. With the help of her friends—Dayanna, Ethan, Brenna, and Thomas—she navigates the joys and perils of a forbidden romance. But when a close call at the Founder’s Day Gala threatens to expose them, Josephine must decide if their love is worth the risk, leading to a bittersweet promise that transcends age and time.