She's a high society girl from a wealthy New York family. He's an orphaned boy who came from nothing. Stacey Tudor has loved Jake Stevens ever since the day her brother brought him home from boarding school. After a disastrous romantic encounter in her family's vacation home, the two quickly fall out of touch.

Years later, Stacey is invited to interview her now extremely successful childhood crush and to finish what they began when they were younger. With her history of failed romances and his inability to trust, can they ever make it work?