In the film Ellen Simon's alter ego is Rebecca Trager Lott (played by Elizabeth Perkins), woman who teaches poetry at one of New York's colleges. Her life is shattered with the news about her husband being killed while jogging. Rebecca must find a way to move on and in doing so she receives support from three other women, burdened with their own problems. Rebecca's best friend Sylvie Morrow (played by Whoopi Goldberg) fears that her husband is going to leave her. Rebecca's younger sister Lucy (played by Gwyneth Paltrow) is troubled by virginity. Rebecca's stepmother and successful businesswoman Alberta (played by Kathleen Turner) can't get over the fact that Lucy and Rebecca still love their deceased mother more than her. In the meantime, Rebecca gets attracted to young and mysterious housepainter (played by Jon Bon Jovi).

MOONLIGHT AND VALENTINO could have served Ellen Simon very well, but the filmmakers and audience weren't that lucky. Hollywood adaptation of the play looks exactly like those Hollywood products that have given bad name to phrases like "chick flick" and "dramedy". Characters are mostly uninteresting and live in fairytale world of American upper middle class, so far away from the average viewers in the theatres. Another problem is utter predictability of the plot - the audience won't have any problems guessing how the film ends and how characters are going to deal with their problems. But the biggest problem for MOONLIGHT AND VALENTINO is its position in the limbo between drama and comedy - the subject is too serious for film to be taken as a comedy, while forced "quirkiness" of the characters take away its credentials of drama. Director David Anspaugh, torn between those two worlds, is unable to find proper direction for this film. The general impression of MOONLIGHT AND VALENTINO is, on the other hand, salvaged by diverse and talented cast, among which Gwyneth Paltrow is the best, and rock star Jon Bon Jovi the most interesting actor. However, although MOONLIGHT AND VALENTINO is watchable, the viewers would probably feel that the better use could have been found for that many talents.