Living Out Loud (1998)

Synopsis
Noted screenwriter Richard LaGravenese made his directorial debut with this dramatic comedy about two unlikely people who find each other while looking for love. Judith Nelson (Holly Hunter) is suddenly single after discovering her husband of fifteen years, a successful doctor (Martin Donovan), has been having an affair with a younger woman. Judith stews, plans, plots and fantasizes, but she can't decide what to do with her life until she goes out to a night club to see singer Liz Bailey (Queen Latifah), who is full of advice on life and love. While out on the town, Judith is suddenly kissed by a total stranger, which opens her eyes to new possibilities ... which is when she notices Pat (Danny De Vito), the elevator operator in her building. Pat's life is in even worse shape than Judith's; his wife has thrown him out for gambling, he's in debt to loan sharks, he's sleeping on the couch of his more successful brother, and his daughter is dying. At first Pat borrows money from Judith, but when the two start talking, they realize they have more in common than they imagined. LaGravenese based his screenplay on a pair of short stories by Anton Chekhov. ~ Mark Deming, All Movie Guide