Synopsis

Stella Payne, a successful but overworked San Francisco financial executive, travels to Jamaica with her friend Delilah for a long-awaited vacation. There she meets Winston Shakespeare, a younger resort employee whose warmth and attention challenge Stella's guarded view of romance. As their relationship deepens, Stella must confront the age difference, her responsibilities, and the fear that starting over means surrendering control of her carefully managed life.

Factoids & Trivia

• The film adapts Terry McMillan's 1996 bestselling novel, with McMillan and Ron Bass credited for the screenplay.

• McMillan's real-life romance with Jamaican hotel worker Jonathan Plummer inspired the novel. Plummer makes a brief appearance in the film as a man welcoming Stella and Delilah to Jamaica.

• The production filmed from September 29 through December 17, 1997. Although Jamaica supplies the story's central setting, filming also took place in California, including San Francisco, Glendale, and Altadena.

• Taye Diggs made his feature-film debut as Winston Shakespeare. The role helped establish him on screen after his stage work.

• Danny Glover was originally intended to play an older man pursuing Stella. Most of his material was removed, although a distant glimpse of Glover in old-age makeup remains in the poolside sequence.

• Released on August 14, 1998, the film earned approximately $39.3 million worldwide against a reported $20 million budget.

• The accompanying soundtrack blended contemporary R&B, hip-hop, and reggae. It reached No. 8 on the Billboard 200 and was certified gold by the RIAA.