Stella is a 40-year-old, high-powered stock broker, workaholic, and dedicated single mom from San Francisco. She is so obsessed with her career and family, she has forgotten how to be romantic, have fun, and take chances. The object of Stella's affections - and dilemma - is Winston Shakespeare, a Jamaican 20 years her junior and young enough to be her son. Stella, played by Angela Bassett, embarks on a relationship that leads her to question not only her concept of love, but the very way she's led her life.