Stella Payne is a very successful 40-year-old stockbroker raising her son, Quincy, and living in Marin County, California, who is persuaded by her best friend from college, Delilah Abraham, to take a well-deserved, first-class vacation to Montego Bay, Jamaica. As she soaks in the beauty of the island, she encounters a handsome young islander, Winston Shakespeare, who is twenty years younger. His pursuit of her turns into a blossoming romance that forces Stella to take personal inventory of her life and try to find a balance between her desire for love and companionship, and her responsibilities as a mother and corporate executive.