From Chicago to New York, 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 women in the world, he's 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 to Deacon's engagement party, Charlie finds him stranded and looking to catch a ride on her family jet. It's an engagement party like any other Winchester affair: extravagant, isolating, and heartbreaking. But 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.