Stella (Angela Bassett) is a wealthy San Francisco stockbroker who lives with her young son in a fancy house overlooking the city. She is a workaholic who has never learned how to nurture herself. On an impulse, Stella asks her best friend Deliah (Whoopi Goldberg) to accompany her on a getaway trip to Jamaica. There, much to her surprise, she is swept off her feet by Winston (Taye Diggs), a handsome, sweet, and sexy Jamaican. They hit it off but face a huge hurdle in taking their relationship to a deeper level — Stella is 40 and Winston is only 20.
Most of this romantic comedy directed by Kevin Rodney Sullivan revolves around the challenges these two have to deal with when they return together to San Francisco. Their families and friends either doubt or disregard the possibility that they could be truly in love. They have totally different generational attitudes toward work, entertainment, and food. She's well-established in a lucrative business but doesn't feel satisfied; he is not sure whether to go to medicine school or pursue another path.
While Stella keeps operating out of her head, Winston listens to his heart. He supports her dreams and honors all her feelings. He offers her the nurturing she refuses to give herself. For instance, when she loses her job and plunges into a funk, Winston says, "I will do your weeping for you, so hush." This fine and funny film proves that a love that nurtures fills an emptiness that nothing else can fill.