When her son leaves to spend two weeks with her ex-husband, Stella (Angela Bassett), a workaholic stockbroker, takes a Jamaican vacation with her best friend Delilah (Whoopi Goldberg). There she meets Winston (Taye Diggs), a sexy 20 year-old man who doesn’t mind the fact that she is twice his age. Although hesitant at first, Stella soon is enjoying her burgeoning relationship with the Jamaican native. Even after returning to San Francisco, she can’t seem to get Winston out of her head or heart. This results in a second Jamaican vacation, this time with her son and niece. After this romp, it takes the death of Stella’s friend to bring Winston to the states. Can they find happiness together or is the age difference just too big a hurdle to overcome?
This romantic drama is so cliched and predictable that the only thing that sets it apart from others of its kind is the playful banter between Stella and her various friends. The casting of Whoopi Goldberg was a mistake, though, as her style of humor jars the viewer into treating the film as light comedy whenever she’s on screen. Angela Bassett is a tremendously talented performer and a constant delight on screen; however, the script here brings her little challenge with its all-too-familiar plot points. If you’ve ever seen an older-woman-younger-man romance on film, there’s no need to see "How Stella Got Her Groove Back"; you’ve seen it before and, probably, better.