Lucy Kelson (Sandra Bullock) is an intelligent, highly competent liberal lawyer who specializes in historic preservation, 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 naïve. Lucy's hard work and devotion to others contrasts sharply with George's childish recklessness and greed.
Lucy meets George in an attempt to stop the destruction of the Coney Island community center from her childhood. Discovering she graduated from prestigious Harvard law school, he offers to hire her to replace his old Chief Counsel, overlooking their opposing views of real estate development. She decides the benefits he offers for discretionary funding for community causes she espouses outweighs the negatives, especially as he promises to protect the community center.
Soon, she finds what he really requires is advice in all aspects of his life. She regretfully becomes his indispensable assistant, and he calls her for every little thing at all hours. 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" he needs her advice on is his attire 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 he can keep her on. Eventually, he gives in, and she offers to help him find a replacement, but unaware 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 June lacks real estate experience. When George sees June he is immediately attracted and is ready to hire her on the spot, with seemingly disregards 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. When George invites June to business social events that formerly would be just between George and Lucy, Lucy increasingly perceives the business events to be more like dates, and is surprised June is intruding on them.
Lucy finds out despite George's promise, the community center is going to be knocked 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 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 his time with her has demonstrated he needs to change. Meanwhile, in her new job, Lucy finds she misses him. He goes in search for her 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.
Hugh Grant as George Wade
Sandra Bullock as Lucy Kelson
Alicia Witt as June Carver
Francie Swift as Lauren Wade
Dana Ivey as Ruth Kelson
Robert Klein as Larry Kelson
Jason Antoon as Norman
Heather Burns as Meryl Brooks
David Haig as Howard Wade
Dorian Missick as Tony
Joseph Badalucco Jr. as Joseph Badalucco
Jonathan Dokuchitz as Tom Brooks
Sharon Wilkins as Polly St. Clair
Bill Bowers as Mime
Adam LeFevre as RV Man
Veanne Cox as Melanie Corman
Janine LaManna as Elaine Cominsky
Iraida Polanco as Rosario
Charlotte Maier as Helen Wade
Katheryn Winnick as Tiffany
Donald Trump as himself
Norah Jones as herself
Mike Piazza as himself