Flipper Purify, played by Wesley Snipes, is a devotedly married African American man thriving in his career at an architectural firm in New York City. His life takes an unexpected turn when an Italian American woman, Angela "Angie" Tucci, portrayed by Annabella Sciorra, is brought on board as a temporary secretary. Flipper expresses his dissatisfaction to his partners, Jerry (Tim Robbins) and Leslie (Brad Dourif), desiring an African American secretary, but they insist on hiring "the best human being for the job."
Upon returning to his Harlem home after a visit with his close friend Cyrus (Spike Lee), Flipper shares the news of his promotion with his wife, Drew, played by Lonette McKee. Although Drew urges him to remain cautious in case his promotion gets revoked, Flipper reassures her not to stress about it. Meanwhile, Angie heads back to her home in Bensonhurst, where she prepares dinner for her father Mike (Frank Vincent) and her two brothers, Charlie (David Dundara) and Jimmy (Michael Imperioli). Her boyfriend, Paulie Carbone, played by John Turturro, arrives to take her out for a date. Paulie, a regular Italian-American man working at a grocery store, faces antagonism from Angie's brothers, who threaten him over his intentions with Angie.
As night falls, Flipper and Angie find themselves working late at the office, which leads to a casual conversation about cooking. Their work atmosphere shifts, culminating in a dinner within his office, resulting in a compromising moment on his desk. The subsequent day, Flipper walks his daughter silently to school, reflecting a new tension in his life. At the office, he voices his desire to become a partner, but after his request is dismissed, he makes the impulsive decision to quit, asserting that his contributions have significantly benefited the firm. Leslie suggests they require "a little more time," while Jerry reacts angrily to his resignation, implying it's Flipper's ego that's dictating his choices.
Later that evening in the park, Flipper confesses his unfaithfulness to Cyrus. Their discussion is disrupted by the sudden arrival of Flipper's older brother, Gator, portrayed by Samuel L. Jackson, who begs Flipper for cash to sustain his drug habit. Despite a moment of resistance, Flipper ultimately succumbs to familial obligation.
Meanwhile, Angie confides in her friends about her relationship with Flipper, shocking them when she discloses his race. Despite her plea for secrecy, the gossiping continues, inevitably reaching her brothers and father Mike. The following evening, Flipper and Angie experience blatant hostility from the restaurant staff due to their interracial relationship. Flipper's complaint to an African-American waitress (Queen Latifah) only elicits a reprimand for his choice in partners. Returning home, Flipper finds a furious Drew tossing his belongings from the window, leading him to temporarily move back in with his parents, Lucinda (Ruby Dee) and the Good Reverend Doctor (Ossie Davis).
As tensions heighten, Flipper confronts Cyrus over the betrayal regarding their private matters, only to discover that Cyrus's wife Vera has spread rumors, straining their friendship. Flipper's anger leads to his definitive break with Cyrus as he grapples with the idea that loyalty lies with family, regardless of their judgment.
In a bid to reconcile with Drew, Flipper brings her flowers at her workplace, only to have them rejected amid a heated argument. At the same time, Angie chooses to end her relationship with Paulie, who receives emotional support from his father Lou (Anthony Quinn) after his heartbreak. Upon returning home, Angie faces violence from her father Mike for dating a black man, leading her to move in with Flipper.
Their cohabitation brings its set of challenges, especially when a dinner with Flipper's parents reveals their disapproval of their son's interracial relationship. As societal pressures mount, their relationship becomes increasingly strained. A pivotal moment occurs when two police officers, Officer Long (Rick Aiello) and Officer Ponte (Miguel Sandoval), nearly arrest Flipper after a false report claiming a white woman is in distress, misinterpreting their relationship.
When Angie confesses her romantic involvement with Flipper to Paulie, he becomes devastated, spurring him to seek connection with a black female regular customer named Orin Goode (Tyra Ferrell). However, familial racism complicates his pursuits, leading to conflicts with his friends and disappointing outcomes even when he persists.
As the story unfolds, a desperate Gator invades his parent's home, demanding money, resulting in a violent confrontation with the Reverend. In a moment riddled with tension, the Reverend inflicts a life-altering injury on Gator, who passes away in Lucinda's arms.
Ultimately, Flipper acknowledges the superficiality underlying his relationship with Angie, leading to a poignant breakup where they both recognize their mutual curiosity regarding interracial dating. Returning home, Angie apologizes to her father for the turmoil her relationship has caused.
In the end, Flipper finds himself in a questionable position with Drew once more, engaging in an intimate encounter despite the unresolved issues between them. As he leaves, he bids farewell to his daughter, Ming (Veronica Timbers), before experiencing a shocking encounter with a young girl soliciting him for sex, provoking a visceral reaction of horror. This confrontation serves as a haunting reminder of the cyclical nature of their struggles, leaving the audience to contemplate the deeper implications of their journey.
