The film is set among New York's black community; all the main characters are black, with white actors seen only in minor roles. (Is this revenge for the way in which Hollywood used to discriminate against black actors?) The title character Woo (this is presumably a nickname although we never get to find out her real name) is a beautiful young woman who is having difficulties in her love-life, and accepts a blind date with a young man named Tim, largely because he is a Virgo. (Her astrologer has told her that she is fated to find romance with someone of that particular star sign).
This is an example of that classical romantic comedy plot, love blossoming between two people of different temperaments. The shy, diffident Tim, a law clerk, is having even more difficulties with his love-life than is Woo; he lacks a social life to such an extent that his friends nickname him Macaulay Culkin (because he's always home alone). Woo, by contrast, is an outgoing, extrovert party animal, and is keen to take Tim out for a night on the town. As this is a romantic comedy, we know that there will be a happy ending; the interest of such films lies in the route taken to reach such an ending. Unfortunately, in this case the route taken is an uninteresting one. We quickly realise just why Woo, despite her physical beauty, has not had great success with men; the woman is spoilt, wilful and a prize bitch, the sort of person who (in one of the film's most manic scenes) wrecks an Italian restaurant after a trivial quarrel with a waiter. It hardly seems credible that Tim would tolerate such an annoying and unlikeable character, let alone conclude that she was the love of his life. He is evidently even more frustrated than we realise. I am not sure whether the problems with Woo's character are the fault of the scriptwriter or of the actress, Jada Pinkett Smith. Probably a mixture of both.
The film has been criticised for allegedly perpetuating stereotypical images of young black males. The character of Tim, in fact, seems to have been designed to get as far away from these stereotypes as possible- he is quiet, middle-class and lacking in self-confidence, especially where women are concerned. The other male characters, however, are written in a stereotypical way, presumably deliberately so in order to accentuate the contrast with the untypical Tim. They are loud, outgoing and streetwise, sexist in their attitudes towards women and prejudiced towards gays. These characters did, however, provide some of the more amusing scenes, which mostly had little to do with the main plot, like the scene in the gay bar where one of the men mistakes transvestites for real women (an old joke, going back at least to "Crocodile Dundee"), or the "Chickie Ho" scene where a man makes his girlfriend dress up as a chicken while making love. (She, unfortunately, is allergic to the feathers and can't stop sneezing). Unfortunately, amusement is in short supply, and the film as a whole makes for pretty dull viewing, a sort of romantic comedy version of those old blaxploitation action films from the seventies. 4/10