Unlucky-in-love stockbroker Stella (Angela Bassett) jets to Jamaica with her gal pal Delilah (Whoopi Goldberg) for some fun in the sun. There, the 40-year-old working woman has an island fling with Winston (Taye Diggs) -- a handsome 20-something. When it's time to return to California, Stella realizes that she's developed real feelings for her new man. But, with their distance from each other, not to mention their disparity in age, does a real relationship stand a chance?