Stella, a divorced Black woman in her 40s takes some time off work and travels to Jamaica while her son spends time with his father. While she is successful in her high-powered job, her love life is non-existant and her friend Delilah persuades her to take a rare vacation in order to relax. There she meets and falls in love with Winston, who is half her age. When Winston takes a time-consuming job, Stella returns home, only to discover she has lost her job. She returns to Jamaica, finding that Winston is in fact much richer than he has let on, but is then called to New York, where Delilah is ill. Winston follows her to New York and the two try to decide if their relationship can work.