Originally cast as the old man who hits on Stella Payne during her initial stay in Jamaica, all of Danny Glover's scenes were deleted from the final cut. He's seen briefly in this movie during the scene where Stella, submerged in a pool, is talking to Winston Shakespeare (who's standing poolside), and points out an older man who's been hitting on her during her stay. In a quick long shot, Glover can be seen in old age make-up holding a flower he intends to give to Stella.
The movie/book was based on author, Terry McMillan's true story. The character, Winston Shakespeare was based on Terry's then-husband, Jonathan Plummer, who has a cameo in this movie. After Stella checks in, she and Delilah walk down some steps and Jonathan can be seen saying, "Welcome to Jamaica, ladies."
Taye Diggs was performing in the Broadway production of "Rent" when he learned that he had landed the male lead in this movie. He celebrated by streaking through the theater where he was working.
The movie was based on a book by Terry McMillan who wrote about her own life and marriage to Jamaican Jonathan Plummer in 1998. She was in her late forties and he in his early twenties. In December 2004, Plummer told McMillan that he was gay, and in March 2005, she filed for divorce. He essentially only married her so he could leave Jamaica and gain American citizenship.
Angela Bassett's Stella Payne and Taye Diggs' Winston Shakespeare ranked number ten on Moviefone's "The Top 25 Sexiest Movie Couples" (May 2008).