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 40s and he in his early 20s. 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.
Originally cast as the old man who hits on Stella during her initial stay in Jamaica, all of Danny Glover's scenes were deleted from the final cut of the film. He's seen briefly in the film during the scene where Stella, submerged in a pool, is talking to Winston (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.
Angela Bassett was planning her nuptials with then-fiancé Courtney B. Vance when cast in the lead role. The start of production kept being pushed back by producer Deborah Schindler which was a blessing and a curse for Bassett. The continued delay of production gave her ample time to get her body in perfect shape for the film but it also prevented her from being able to set a definite date for her wedding. Determined to get married in the fall of 1997, Bassett and Vance stood their ground and set a firm date for the ceremony, October 17, 1997, by that point Bassett had been filming for about a month on "Stella."
In March 2007, Terry McMillan sued her ex-husband Jonathan Plummer and his lawyer for $40 million, citing an intentional strategy to embarrass and humiliate her during the divorce proceedings. McMillan eventually won a judgment of intentional infliction of emotional distress but had withdrawn the suit before the case went to trial and Plummer was never ordered to pay the intended amount. On September 27 2010, the two sat together with Oprah Winfrey on Oprah Winfrey to discuss their post-divorce relationship and partial reconciliation and both acknowledged that he fulfilled the role of boyfriend and husband before his coming-out although McMillan stated that 'he's not my BFF'.
The movie/book is based on author, Terry McMillan's true story. The character, Winston Shakespeare is based on Terry's then husband, Jonathan Plummer, who has a cameo in the movie. After Stella checks in, she and Delilah walk down some steps and Jonathan can be seen saying, "Welcome to Jamaica, ladies."
Taye Diggs plays 20 year old Winston Shakespeare to the significantly older woman's character, Stella Payne (Angela Bassett). Angela Bassett is only 13 years older than Diggs who is actually 27 years old in this movie.