A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him.
Harvard educated lawyer Lucy Kelson, following in the footsteps of her lawyer parents, uses her career for social activism. She hides any sense of femininity behind her work. George Wade is the suave public face of the Manhattan-based Wade Corporation, a development firm that Lucy routinely opposes and whose true head is George's profit-oriented brother, Howard Wade. George, who has a reputation as a lady's man, has had as his legal counsel a series of beautiful female lawyers with questionable credentials, they who have more primarily acted as his casual sex partners. Needing a real lawyer, he offers Lucy the job of his legal counsel on a chance meeting. Despite warnings from her parents in working for the "enemy", Lucy, who has no intention of being the latest in his bed partners, accepts the job as she feels she can do more good from the inside, and as George, as part of the job offer, promises not to demolish a community center in a heritage building as part of a development project near her childhood Coney Island home where her parents still live. Although Lucy is able to effect the type of change she wanted from this position, she finds she cannot deal with George's expectations of her, namely being his primary confidante and advisor at all hours of the day and night, mostly about issues she considers frivolous. As such, she gives him two weeks notice, although she promises to help George find her replacement. As Lucy begins to review resumes, George himself unilaterally decides to hire June Carver, a fellow Harvardite, but who seems to have her sights set on George as both a boss and personal partner. As June begins to replace Lucy in seemingly all aspects of George's life, Lucy begins to realize that she herself has fallen for George. However, Lucy's feelings for George and her attempts to re-ingratiate herself into George's life are placed into jeopardy when she learns of a Wade Corporation decision against her basic sensibilities.—Huggo
Lucy Kelson, the brilliant but insecure lawyer with a sharp, strategic mind, is working as a Chief Counsel for the Wade Corporation: one of New York City's most important commercial real estate developers. As a result, she can't get much sleep, and as if that weren't enough, she also has a chronic ulcer. Of course, it's not the job that's getting to her; it's her millionaire boss, George Wade. Handsome, charming, and, irrefutably, self-centred, George treats Lucy more like his nanny than a well-trained Harvard Law graduate, and what's even more impressive, he can barely choose a tie without her help. Now, after one long year of calling the shots--pretty much on everything, from his clothes to his divorce settlements--Lucy Kelson is finally calling it quits. But, Wade is given two weeks notice. Is it ever too late to say "I love you"?—Nick Riganas
Lucy Kelson (Sandra Bullock) is an intelligent, highly competent (Harvard educated) liberal lawyer who specializes in historic preservation (she gets on top of wrecking balls to prevent them from being used on historical buildings in the city), environmental law, and Pro Bono causes in New York City. George Wade (Hugh Grant) is an arrogant, needy billionaire real estate developer and stylish womanizing playboy, who is also quite naive. Lucy's hard work and devotion to others contrasts sharply with George's childish recklessness and greed.
Lucy's parents Ruth Kelson (Dana Ivey) & Larry Kelson (Robert Klein), have to constantly bail her out of jail, when she runs afoul of the authorities. Howard Wade (David Haig) is George's brother & Helen Wade (Charlotte Maier) is his prim and proper, micro-controlling wife. Howard is angry with George for losing good business deals as George continues to employ models as lawyers, who don't know how to do their job. Howard gives an ultimatum to George to hire a real lawyer within a day.
Lucy meets George in an attempt to stop the destruction of the Coney Island community center from her childhood (George does point out that Trump property developers also have an inside track on the Coney Island project and saving the community center will be difficult. But Lucy guarantees the project to Wade, if he promises to save the center). Discovering that she graduated from prestigious Harvard law school, he attempts to hire her to replace his old Chief Counsel, overlooking their opposing views of real estate development. She decides that the benefits he offers for discretionary funding for community causes she espouses outweighs the negatives, especially as he promises to protect the community center.
She soon finds that what he really requires is advice in all aspects of his life (which stationery design, mattress for the house). Within 10 months, she regretfully becomes his indispensable aide, and he calls her for every little thing at all hours. Lucy manages to negotiate very good terms with George's ex-wife for the divorce settlement, but George walks in and gives her what she wants, despite the fact that she cheated on George. Lucy feels like George is not allowing her to do her job.
At a friend's wedding, her cell phone loudly rings and disrupts the proceedings before she responds to his urgent page. When she discovers the "emergency" is he needs her advice on what to wear to an important event, she gives him her two weeks' notice of resignation. Yet, her departure is not so easy.
Lucy looks for work at other firms, but everyone says no because George has called in advance asking them not to hire her, so that he can keep her on. George points out that Lucy herself drafted her contract that says that she will work for George till the Coney Island project is built. Her parents are also lawyers and say that the contract is iron clad. Lucy decides to get fired from her job and acts very recklessly in front of Howard and George.Eventually he gives in, and she offers to help him find a replacement, but the camera shows us that they are not entirely aware of how close and interdependent they have become: they act like an old married couple at a restaurant, able to simultaneously carry out a conversation while involuntarily exchanging food out of habit from knowing each other's food preferences.
When potential interviewee June Carver (Alicia Witt) shows up without an appointment seeking the position, Lucy speaks to her, but is concerned that June lacks real estate experience. When George sees June, he is immediately attracted and is ready to hire her on the spot, with seemingly little regard for Lucy's concerns. Rather than look the other way and let her soon-to-be-former boss deal with the foolishness of his sexist hiring practices, Lucy instead becomes increasingly concerned and competitive with her replacement (At a friendly tennis match, they end lobbing balls at each other's bodies). When George invites June to be included to business social events that formerly would be just between George and Lucy (he invites June to a charity event), Lucy increasingly perceives the business events to be more like dates and is surprised that June is intruding on them.
Lucy finds out that despite George's promise, the community center is going to be knocked down (Howard called George to tell him that due to the center, the construction costs are out of control, and it will be way cheaper to just knock it down) and challenges him on his apparent betrayal. She arrives at his hotel to confront him and finds June and George in his apartment in lingerie during a game of "strip chess". George confronts her the next day, her last day, where Lucy reminds him that he promised her to spare the community center. Lucy leaves after George accuses her of being a saint, making everyone else look bad because they are humans who make mistakes.
After she is gone, George realizes that his time with her has demonstrated that he needs to change. Meanwhile, in her new job, Lucy finds she misses him. He goes in search for her (he comes to her office at Legal Aid) and reveals he decided to keep his promise to her. Lucy initially rebuffs him but then returns and they declare their feelings. George reveals he resigned.In the DVD version of the film, an unreleased wedding scene of George and Lucy was featured. George and Lucy were married at the community center attended by family and friends.The movie ends with Lucy ordering take out in her apartment with George making jokes about the size of the apartment. Usually when she orders and is asked how many, Lucy replies, "one," but this time, with a sly smile, Lucy replies, "this is for two."
