Lucy Kelson, an intelligent and highly proficient Harvard-educated lawyer, is deeply committed to historic preservation, environmental law, and various pro bono causes in the bustling city of New York. In stark contrast, George Wade, portrayed by Hugh Grant, is an arrogant, self-serving billionaire real estate developer with a flair for style and a penchant for womanizing, yet he remains somewhat oblivious to the consequences of his actions.
Lucy finds herself often at odds with George's childish carelessness and relentless greed. Her parents, Ruth (Dana Ivey) and Larry (Robert Klein), frequently have to come to her rescue, often bailing her out of jail as she stands up against the authorities to protect what she holds dear. George's brother, Howard (David Haig), is frustrated with George's inability to make sound business decisions, especially as George hires incompetent models disguised as lawyers. Howard eventually issues an ultimatum, insisting George hire a competent attorney within a day.
Upon meeting George in her efforts to save her cherished childhood community center at Coney Island, Lucy becomes entangled in a partnership that starkly contrasts her principled morals with George's casual approach to business. Despite their differences, George decides to hire Lucy as his chief counsel, overlooking their conflicting views on real estate development. Lucy rationalizes her decision, thinking that the discretionary funding he offers for community initiatives justifies the means, especially since he promises to protect the community center.
As time passes, Lucy quickly becomes George's indispensable aide, answering his every small request, from choosing stationery to selecting mattresses. After managing a favorable divorce settlement with George's ex-wife, Lucy comes to realize that George is stifling her ability to work effectively. During a friend's wedding, his ringing cellphone disrupts the celebration, and when Lucy discovers that the "emergency" is merely his fashion dilemma, she decides it's time to resign. However, her exit proves complicated.
When she seeks new employment, Lucy finds doors closing thanks to George’s preemptive calls to other firms advising them against hiring her. A daunting reality dawns on her; the contract she drafted to work until the Coney Island project is completed is ironclad, with her parents advising her against termination. Frustrated, Lucy makes a reckless attempt to get fired, pushing George beyond his limits. They unwittingly slip into habits akin to an old married couple, effortlessly understanding each other’s subtle cues.
As new contender June Carver, portrayed by Alicia Witt, steps into the mix, Lucy's competitive instincts kick in as she worries about George’s instant attraction to her. When George begins inviting June to social events that were once shared solely with Lucy, it creates a sense of jealousy and rivalry.
Just when Lucy feels betrayed by George's decision to prioritize cost-cutting over the community center, she confronts him only to catch him with June during an intimate moment. With emotions running high, they argue, and Lucy exits, stung by George's reluctance to make the right choices.
In the wake of her departure, both realize their strong connections and the changes they have inspired in each other. George, understanding the depth of his feelings and regretting his earlier actions, seeks Lucy out at her new job, expressing his commitment to her original pledge about the community center. Initially resistant, Lucy ultimately acknowledges her feelings for him.
In a heartwarming conclusion, George reveals that he has stepped down to fulfill his promise, thereby beginning a new chapter together. An unreleased wedding scene in the DVD edition adds a charming touch, showing them marrying in the community center surrounded by loved ones. The film closes with an intimate moment shared between Lucy and George in her apartment, humorously ordering takeout and signifying their newfound partnership as Lucy, with a playful smile, announces that the order is "for two."
