Flipper Purify (Wesley Snipes) is a successfully married African American man who works at an architectural firm in New York City. One day, an Italian American woman named Angela "Angie" Tucci (Annabella Sciorra) is hired as a temporary secretary at the place. Flipper complains to his partners Jerry (Tim Robbins) and Leslie (Brad Dourif) about wanting an African American secretary. They tell him that they want "the best human being for the job."When Flipper returns to his Harlem home after visiting his best friend Cyrus (Spike Lee), he tells his wife Drew (Lonette McKee) about his promotion. Drew tells him to be prepared if his promotion is declined, but Flipper tells her not to worry. Meanwhile, Angie returns to her Bensonhurst home, and cooks dinner for her father Mike (Frank Vincent) and her two brothers Charlie (David Dundara) and Jimmy (Michael Imperioli). Her boyfriend Paulie Carbone (John Turturro) arrives and takes her out on a date. Paulie is a regular Italian-American man who co-manages a grocery store in his and Angie's neighborhood. While he waits for Angie, her brothers antagonize Paulie about his relationship with his sister, threatening him with bodily harm if his only intention is to have sex with her. Paulie's able to shake it off and he & Angie leave. One night, Flipper and Angie are working late at the firm, and they start to have a conversation about cooking. They continue to work late and have dinner in his office and they have sex on a desk. The next day, Flipper doesn't speak while walking his daughter to school. Later, at the office, he tells Jerry and Leslie that he wishes to be made a partner at the firm. After his offer is declined, he abruptly quits his job, telling his employers that his ideas have made the firm very profitable. One of his bosses, Leslie tells Flipper they need "a little more time" while Les' partner, Jerry, reacts angrily to Flipper's resignation, saying that his ego is driving his decisions. Later that night at the park, Flipper admits his infidelity to Cyrus. Just then, Flipper's older brother Gator (Samuel L. Jackson) shows up with his girlfriend Vivian (Halle Berry). He asks Flipper for some money so he can feed his crack habit. Flipper initially refuses, but gives in eventually.Meanwhile, Angie tells her two girlfriends that she's seeing Flipper, shocking them when she tells them he is African American. She then tells them not to tell anybody. But her friends just cannot stop their gossiping and they secretly tell one of Angie's brothers, who likewise, tells their father Mike.The next evening, Flipper and Angela are ignored by the racist staff at a local restaurant. He complains to an African-American waitress (Queen Latifah) about not being served, she in turn berates him for dating a white woman. Later, the rumors about them surface when Flipper comes home and sees a furious Drew throwing his things out of the second floor window, forcing him to move back in with his mother Lucinda (Ruby Dee) and his father the Good Reverend Doctor (Ossie Davis) in nearby Brooklyn. Later that night, he confronts Cyrus for betraying his trust. Cyrus admits that he told his wife Vera (Veronica Webb), but he didn't know that she would tell Drew (plus several other people in the neighborhood). Flipper insults Vera for her big mouth and inability to keep a secret which causes a rift in his friendship with Cyrus, who demands he apologize to Vera, but Flipper refuses. Shortly after, Flipper ends his friendship with Cyrus after seeing that although Cyrus does like and support Flipper, he will always side with his wife regardless of her actions.The next day, Flipper tries to make things up to Drew by bringing her flowers at work, which she refuses. The two have a nasty argument and Flipper leaves. Meanwhile, Angie ends her relationship with Paulie. His father Lou (Anthony Quinn) finds Paulie in the bathroom and consoles him. When Angie returns home, a livid and racist Mike violently beats her for dating a black man and throws her out of the house.Flipper and Angie move in to an apartment together, where they subsequently encounter social problems including a failed dinner with Flipper's parents who disapprove of their son dating someone outside his race. These and other racial issues eventually strain relations between the couple. One night, things come to a head when the police almost arrest Flipper after receiving a wrongful report from another racist white person that "a white lady was being attacked" (this, due to somebody apparently having watched them in a compromising position over a car hood from a window, since it looked like he was forcing himself on her). Afterword, Flipper and Angie get into another huge argument when he tells her that he refuses to have half-blood children with her.When Paulie hears the confession from Angie about her affair with a black man, he is heartbroken. This, somehow, gives him the courage to ask a black female regular customer, named Orin Goode (Tyra Ferrell), out on a date. This puts him at odds with his own racist father and his friends, whom he gets into a fight with, although he winds up hurt himself. Orin turns down Paulie's request to go out on a date. When he pesters her, Orin tells him off by saying that her parents have forbidden her from dating a man outside her race and she will not defy her parents out of blind loyalty to them. Paulie finds himself more emotionally hurt and alone then ever.One night, a high-on-dope Gator storms into his parents house one night while the Reverend is away, demanding money from Lucinda while trashing the house. The Reverend arrives and threatens to shoot him if he doesn't leave. Gator turns to leave, but upon hearing the Reverend insult him, he turns around and threatens him. The Reverend tells Gator he is better off dead, and shoots him in the groin. Gator cries in pain as he slowly dies in his mother's arms. However, The Reverend shows a small sign of regret.Eventually, due to the great gap created between them two, Flipper admits that he was only curious about being with a white woman, and he tells Angie that she should accept she was also curious about black men. They break up and he leaves the apartment they were sharing. Angie returns to her father's house where she apologizes for getting into a romance with a man who's color skin is different. Mike awkwardly welcomes Angie back.In the end, Flipper is seen having sex with Drew again, but she is laughing and crying at the same time. When they finish, she sends him off. It is clear that they were obviously not back together and she only called him over for sex, with no seemingly immediate solution in regards to it. He kisses his daughter Ming (Veronica Timbers) goodbye and walks out to go home back to his parents house. Then, at the turn of the corner, a very young black girl asks him to let her do oral sex on him for two dollars. Stunned, Flipper embraces her and screams to the heavens: NOOOOOOO!!!!.(It was not clear whether the plot had leaped forward to some years later and this girl was Ming, or that he was only shocked to see this teenager whoring herself for drug money.)