Stella (Angela Bassett) is a very successful, 40-year-old stock broker raising her son and living in San Francisco, California who is persuaded by her New York girlfriend Delilah (Whoopi Goldberg) to take a well deserved, first-class vacation to Montego Bay, Jamaica. As she soaks in the beauty of the island, she encounters a strapping young islander, Winston Shakespeare (Taye Diggs), who is 20 years her junior. His pursuits for her turn into a hot and steamy romance that forces Stella to take personal inventory of her life and try to find a balance between her desire for love and companionship, and the responsibilities of mother and corporate executive.

The character "Winston Shakespeare," (played by Taye Diggs in the movie), is based on McMillan's husband, Jonathan Plummer. Plummer is Jamaican and is more than 20 years younger than McMillan. In June 2005, Plummer announced that he was gay, and McMillan filed for divorce.