From Chicago to New York City, Charlie Winchester has been a rich girl --- and she is still technically a rich girl, even though she's barely on speaking terms with her father. But now she might just be a lost girl. Still reeling after her self-imposed exile, she finds herself plagued by dreams --- or nightmares, depending on who you ask --- of a life with the one person she can't have. Not only is her brother Deacon getting married to one of the most famous supermodels in the world, but he's also expanding the family business and doing it alongside his best friend --- the love of her life and the man whose heart she broke, David. After David misses his flight for Deacon's engagement party, Charlie finds him standing in the back of her classroom looking to catch a ride on her family's jet. The engagement party is like any other Winchester affair: extravagant, isolating and heartbreaking. Charlie strikes up a friendship in the unlikeliest of places --- with Tripp Banks of all people --- and realizes she might just be well and truly adrift.