The Luckiest Girl is the story of Ani FaNelli, a sharp-tongued young woman from New York who seems to have it all: a coveted position at a glossy magazine, flashy clothes, and the prospect of a dream wedding on the island of Nantucket. But when the director of a murder documentary invites her to present her view of the shocking incident that happened when she was a teenager at the prestigious Brentley School, Ani is forced to face a dark truth that threatens to turn her head upside down the life built with so much care.